TREA

ANTIPARASITIC COMPOUNDS

Follow

Information

  • Patent Application
  • 20240315993
  • Publication Number
    20240315993
  • Date Filed
    January 26, 2022
    2 years ago
  • Date Published
    September 26, 2024
    3 months ago
Information
Abstract
The present invention relates to cyclopropylamide compounds that are useful in the treatment of parasitic infestations of animals. The compounds have the formula (I).
Description
FIELD OF THE INVENTION

This invention relates to the use of cyclopropyl amide compounds, compositions and methods for controlling parasitic infestations of animals.


BACKGROUND OF THE INVENTION

A number of parasites are known to infest animals. These parasites can be great nuisances to both the animals and their owners.


Treatment of animals to prevent infestation by parasites, or to reduce or control the proliferation of these parasites, especially ectoparasites of animals such as ticks in animals is thus important.


The compounds currently available for parasite control and especially ectoparasite and tick control do not always demonstrate good efficacy, sufficiently quick onset of activity, or a long duration of action.


Ectoparasites tend to irritate the animals and can also cause clinical disease and adverse sub-clinical conditions, either by themselves or by carrying vector-transmitted pathogens.


Specifically, ticks parasitize on wild as well as domesticated animals and humans, and are known or suspected to be responsible for the transmission of pathogens including bacteria, viruses and protozoan parasites. Ticks also release toxins which cause inflammation or paralysis in the host. Occasionally, these toxins are fatal to the host.


On the other hand, such ectoparasites seriously impact productivity in the livestock animal industry by reducing weight gain, or milk production, causing inferior quality hide, wool, and meat, and in some cases resulting in mortality. Ectoparasites are also responsible, in part, for the spread of pathogens as vectors and cause discomfort in livestock and companion animals impacting animal welfare.


For example, a parasite which is prevalent among livestock animals, such as cattle, is the tick of the genus Rhipicephalus, especially those of the species R. microplus (tropical cattle tick), R. decoloratus and R. annulatus. Ticks such as R. microplus (formerly Boophilus microplus) are difficult to control because they lay eggs in the pasture where animals graze.


Such limitations include toxicity and safety of existing compounds both for the animal and the user/owner, limited efficacy (potency, onset of activity and duration), narrow spectrum of parasiticide action, bioavailability, pharmacokinetics and pharmacodynamics challenges and resistance issues. Further, certain aspects of the invention overcome at least some limitations in the use of current parasiticides, particularly in providing effective long term, safe control of parasites, that are known to be difficult to treat.


International patent applications WO2016/168056, WO2016/168058, WO 2016/168059 and WO2018/071327 disclose certain cyclopropyl amide compounds as having insecticidal and acaricidal activity and therefore, being useful in controlling agricultural plant pests. Although veterinary use is briefly mentioned, none of these citations exemplify or describe their use of the compounds as claimed herein that address at least some of the needs for its use of such compounds as veterinary medicament as described above. Furthermore, it was found that only a small selection of the compounds as described in these citation actually have an effect on veterinary parasites.


SUMMARY OF THE INVENTION

The present invention is related in a first aspect to a compound of Formula (I)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R1 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)IR10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)IR10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)IR10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R11 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





Suitably the compounds of the invention and any embodiments thereof are for use in a method of treatment or control of a parasitic infestation of an animal,


Suitably the compound and use according to invention and/or any embodiment thereof

    • R1 is selected from the group consisting of H F, and Cl;
    • R2 is selected from the group consisting of H, F, and Cl;
    • R3 is selected from the group consisting of H, F, and Cl;
    • R4 is selected from the group consisting of H, F, and Cl;
    • R5 is selected from the group consisting of H F, Cl, Br, and I;
    • R6 is selected from the group consisting of H, F, and Cl, Br, and CH3;
    • R7 is selected from the group consisting of H F, Cl, Br, and I;
    • R8 is selected from the group consisting of H, F, Cl, and Br, and CH3;
    • R9 is selected from the group consisting of H F, Cl, Br, and I;
    • R11 is H;
    • R12 is selected from the group consisting H, F, CL, CH3, CF3;
    • R13 is selected from the group consisting of H, F, Cl, CF3 and CH3;
    • R14 is H or F;
    • R15 is selected from the group consisting of H and CH3.


Suitably the compound and use according to invention and/or any embodiment thereof

    • R1 is H;
    • R2 is selected from the group consisting of H, F, and Cl;
    • R3 is selected from the group consisting of H, Cl, F, and Br;
    • R4 is H, F, Cl;
    • R5 is selected from the group consisting of H F, and Cl;
    • R6 is selected from the group consisting of H, F, and Cl, and CH3;
    • R7 is selected from the group consisting of H F, and Cl;
    • R8 is selected from the group consisting of H, F, Cl, and CH3;
    • R9 is selected from the group consisting of H F, and Cl;
    • R11 is H;
    • R12 is selected from the group consisting H, F and Cl;
    • R13 is selected from the group consisting of H, F, and Cl;
    • R14 is H;
    • R15 is selected from the group consisting of H and CH3.


Surprisingly it has been found that the compounds described in this application can be used as medicaments, especially as veterinary antiparasitic medicaments to treat or control parasite infestation of animals.


The invention is understood to include compounds of the invention and/or embodiments thereof as described in this application for use as a medicament, especially a veterinary medicament, more preferably an antiparasitic veterinary medicament.


The invention is also understood to include the use of compounds of the invention and/or embodiments thereof as described in this application in the manufacture of a medicament for the treatment or control of parasite infestation of animals.


The invention is also understood to include the use of compounds of the invention and/or embodiments thereof as described in this application in the manufacture of a medicament for the protection of animals from parasite infestation.


The compounds of the invention and/or embodiments thereof are suitably used in a method to treat or control an ectoparasite infestation.


Suitably the compounds of the invention and/or embodiments thereof are used in a method, wherein the parasitic infestation is a tick infestation or flea infestation. The compounds are suitably used for a tick infestation.


The compounds of the invention and/or embodiments thereof are suitably used against parasites wherein the parasite is a one host tick or a multi-host tick. Suitably the compounds of the invention are used against Rhipicephalus microplus.


In a suitable use or method of the invention and/or any embodiment thereof, the animal is a warm-blooded animal such as a mammal. Suitably, the compounds are also active in a livestock animal, such as a ruminant, bovine animal, or cattle. It was also found that the compounds are active in fish, against a sea lice infestation. Also the compounds are found active in a companion animal, such as a canine animal or a feline animal, especially a dog or cat.


In a suitable use or method of the invention and/or any embodiment thereof, the animal is protected from a parasite infestation. Preferably an existing parasite infestation of the animal is treated or controlled.


In a suitable use or method of the invention and/or any embodiment thereof, the method comprises administering the compound to an animal weekly, bi-weekly, monthly, every 6 weeks, every 2 months or every 3 months.


The invention is also directed to a veterinary composition comprising an effective amount of a compound of Formula (I)-(XCII) as defined in any embodiment described herein and an inert carrier or formulation adjuvant. The composition is suitable for use in the treatment and control of a parasitic infestation of animals such as described herein.


Suitably the veterinary composition is a topical composition, an oral composition, or an injection composition.





BRIEF DESCRIPTION OF THE FIGURES


FIG. 1 shows Plasma concentration of oily solution (Composition A) and volatile solution (Composition B) of compound 453.



FIG. 2 shows a comparison of concentrations of Compound 453 in the blood of cattle with no CPE (Composition C) and three different CPEs (Compositions D, E, and F) showing no significant improvement with the inclusion of any CPE.



FIG. 3 shows the duration of efficacy >90% against R. microplus and the onset of efficacy>90% against R. microplus for Composition G, H and Composition of Example 1.



FIG. 4: Structures of the compounds 1-480.





DETAILED DESCRIPTION

This detailed description of preferred embodiments is intended only to acquaint others skilled in the art with Applicants' invention, its principles, and its practical application so that others skilled in the art may adapt and apply the invention in its numerous forms, as they may be best suited to the requirements of a particular use. This detailed description and its specific examples, while indicating preferred embodiments of this invention, are intended for purposes of illustration only.


This invention, therefore, is not limited to the preferred embodiments described in this specification and may be variously modified. In addition, for conciseness purposes and readability only some combinations of embodiments are explicitly described, however it should be understood that other combinations of embodiments are also contemplated.


Briefly, this invention relates to compounds that can generally be used as active ingredient in a medicament for animals. The compounds of the invention and/or embodiments thereof are suitably used in a method to treat or control an ectoparasite infestation and/or to protect animals from parasite infestations.


Surprisingly, it has been found that the compounds of the invention and/or embodiments thereof described herein exhibit superior broad-spectrum efficacy against harmful parasites more rapidly, and over a long duration compared to other similar compounds known in the art when administered to an animal in need thereof. Therefore, these compounds are useful in the methods or uses of the invention and/or embodiments thereof.


In the following text the compounds for use according to the invention and/or embodiments thereof are described as “compounds of the invention” or “compounds” or “compounds of the invention and/or embodiments thereof (including compounds of Formula (I)” or “compounds of formula (I)” when they are disclosed as compounds per se or as compounds for use/in the method according to the invention.


The unexpected broad parasiticidal properties of these compounds for use according to the invention and/or embodiments thereof are of considerable significance since there are few agricultural pesticides that can be effectively be used against ectoparasites of animals, let alone against a broad range of animal parasites and in various target species


Compounds of the invention and/or embodiments thereof including compounds of Formula (I)-(XCII) show desirable bioavailability and pharmacokinetics when using different administration routes to administer them as a medicament to animals. Many of the compounds also provide desirable safety profiles toward the target host animal and/or their owners. In addition, it has been discovered that a single administration of such compounds generally provides potent activity against a broad range of ectoparasites, including difficult to treat parasite infestations, using relevant administration routes while also tending to provide fast onset of activity, and/or long duration of activity, and/or desirable safety profiles. Consequently, these compounds have been shown to be useful as medicaments, especially antiparasitic veterinary medicaments.


The compounds of the invention and/or embodiments thereof show desired beneficial properties, that makes their use in medicaments for animals suitable and it has been further shown that the resistance breaking properties of such compounds are very favorable.


The Examples show that compounds of the invention and/or embodiments thereof including compounds of Formula (I) have broad activity both in vitro and in vivo against a number of veterinary relevant parasites that affect animals, such as one-host and multi-host ticks, fleas, bed bugs and sea lice that belong to diverse classes of biological organisms that are veterinary relevant parasites. It has been further shown in the Examples that existing parasite infestation with such parasites in different animals (cattle, dogs, fish, guinea pigs) can be successfully treated, while being safe to the animal.


Furthermore, the examples show that the compounds of the invention and/or embodiments thereof act against a broad range of animal parasites, in particular ectoparasites when administered to various target animals using a variety of administration routes.


Consequently, by using the compounds of the invention and/or embodiments thereof as described in this application disadvantages of the prior art can be avoided, because a convenient, safe administration of the cyclopropyl amide compound would be sufficient to achieve the desired effect.


In a first aspect the invention is directed to a compound of Formula (I)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • and wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





It was found that compounds wherein the ring formed by C-A1-A2-A3-A4-A5 is substituted with at least one halogen, these compounds are active against animal ectoparasites. This is in contrast to compounds wherein the ring formed by C-A1-A2-A3-A4-A5 is not substituted with at halogen.


The comparative example below shows that similar compounds have been tested in prior art documents WO2016/168059 and WO2018/071327 against a range of agrochemical relevant parasites. Many compounds from WO2016/168059 and WO2018/071327 that were active in plant protection assays, were not active against animal parasites in an assay as described in Example 1. It was found that compounds wherein the ring formed by A1-A5 that did not have a halogen substitution were active against agrochemical parasites but not against animal parasites. Compounds wherein the ring formed by A1-A5 is substituted by at least one halogen are active against animal parasites.


In the first aspect the compounds according to the invention are further defined as follows

    • R1 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;
    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;
    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;
    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;
    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;
    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;
    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;
    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;
    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;
    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;
    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;
    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;
    • R11 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;
    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;
    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;
    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;
    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl
    • H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl;
    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.


In an embodiment of the invention and/or embodiments thereof, R1 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R1 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R1 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R1 is H.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, ((C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting of H, F, Cl, Br, CN, (C1-C6)alkyl, (C1-C6)haloalkyl and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R2 s selected from the group consisting of H, F, Cl, Br, CN, CH3, CHF2, CF3, OCHF2 and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R2 s selected from the group consisting of H, F, Cl.


In an embodiment of the invention and/or embodiments thereof, R2 s selected from the group consisting of F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R2 is Cl.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R2 is selected from the group consisting of H, F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, ((C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, I, CH3, CF3, CHF2, OCF3, OCH3, CH═CHF, C≡C, CH═CH2.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, and I.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R3 is H or F.


In an embodiment of the invention and/or embodiments thereof, R3 is H.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R3 is selected from the group consisting of H, F, Cl, Br, and I.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, ((C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl (C1-C6)alkoxy, (C2-C6)haloalkenyl, and S-(Halo)5.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, CH3, CF3, OCH3, CH═CHF, C≡C, CH═CH2 and SFs.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R4 is Cl.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R4 is selected from the group consisting of H, F, Cl, Br.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)O(C1-C6)alkyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH—C(═O)O(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, and CF3.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, Br, and I.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R5 is H or F.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)O(C1-C6)alkyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH—C(═O)O(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, and (C2-C6)haloalkenyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, Br, and CH3.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, and CH3.


In an embodiment of the invention and/or embodiments thereof, R6 is H or F.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)O(C1-C6)alkyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH—C(═O)O(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, and (C2-C6)haloalkenyl.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, Br, and I.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R7 is H or F.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)O(C1-C6)alkyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH—C(═O)O(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, and (C2-C6)haloalkenyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, Br, and CH3.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, and CH3.


In an embodiment of the invention and/or embodiments thereof, R8 is H or F.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)O(C1-C6)alkyl, N((C1-C6)alkyl)2, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH—C(═O)O(C1-C6)alkyl.


Compound and use according to any of the preceding claims, wherein R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)alkenyl, and (C2-C6)haloalkenyl.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3, CH═CHF, CH═CH, and CF3.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of H, F, Cl, Br, and I.


In an embodiment of the invention and/or embodiments thereof, R9 is selected from the group consisting of H, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R9 is H or F.


In an embodiment of the invention and/or embodiments thereof, R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—.


In an embodiment of the invention and/or embodiments thereof, R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R6 and R7 is not substituted.


In an embodiment of the invention and/or embodiments thereof, R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—.


In an embodiment of the invention and/or embodiments thereof, R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl.


In an embodiment of the invention and/or embodiments thereof, the ring formed by R7 and R8 is not substituted.


In an embodiment of the invention and/or embodiments thereof, R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl.


In an embodiment of the invention and/or embodiments thereof, R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl.


In an embodiment of the invention and/or embodiments thereof, R11 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, and (C1-C6)alkyl-S(O)2NH2.


In an embodiment of the invention and/or embodiments thereof, R11 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, and (C1-C6)alkyl.


In an embodiment of the invention and/or embodiments thereof, R11 is selected from the group consisting of H, F, Cl, Br, I, and CH3.


In an embodiment of the invention and/or embodiments thereof, R11 is selected from the group consisting of H, F, Cl, and CH3.


In an embodiment of the invention and/or embodiments thereof, R11 is H.


In an embodiment of the invention and/or embodiments thereof, R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, and (C1-C6)alkyl-S(O)2NH2.


In an embodiment of the invention and/or embodiments thereof, R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl; (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R12 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R12 is selected from the group consisting of H, F, Cl, CH3 and CF3.


In an embodiment of the invention and/or embodiments thereof, R12 is H or F.


In an embodiment of the invention and/or embodiments thereof, R12 is H.


In an embodiment of the invention and/or embodiments thereof, R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)alkyl-S(O)2NH2 and triazolyl.


In an embodiment of the invention and/or embodiments thereof, R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.


In an embodiment of the invention and/or embodiments thereof, R13 is Cl or F.


In an embodiment of the invention and/or embodiments thereof, R13 is Cl.


In an embodiment of the invention and/or embodiments thereof, R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, and (C1-C6)alkyl-S(O)2NH2.


In an embodiment of the invention and/or embodiments thereof, R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6)haloalkoxy.


In an embodiment of the invention and/or embodiments thereof, R14 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.


In an embodiment of the invention and/or embodiments thereof, R14 is selected from the group consisting of H and F.


In an embodiment of the invention and/or embodiments thereof, R14 is H.


In an embodiment of the invention and/or embodiments thereof, R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R15 is selected from the group consisting of H, (C1-C6)alkyl, and (C1-C6)haloalkyl.


In an embodiment of the invention and/or embodiments thereof, R15 is selected from the group consisting of H, CH3, and CF3.


In an embodiment of the invention and/or embodiments thereof, R15 is selected from the group consisting of H, and CH3.


In an embodiment of the invention and/or embodiments thereof, R15 is H.


In an embodiment of the invention and/or embodiments thereof,

    • R1 is selected from the group consisting of H F, and Cl;
    • R2 is selected from the group consisting of H, F, and Cl;
    • R3 is selected from the group consisting of H, F, and Cl;
    • R4 is selected from the group consisting of H, F, and Cl;
    • R5 is selected from the group consisting of H F, Cl, Br, and I;
    • R6 is selected from the group consisting of H, F, and Cl, Br, and CH3;
    • R7 is selected from the group consisting of H F, Cl, Br, and I;
    • R8 is selected from the group consisting of H, F, Cl, and Br, and CH3;
    • R9 is selected from the group consisting of H F, Cl, Br, and I;
    • R11 is H;
    • R12 is selected from the group consisting H, F, CL, CH3, CF3;
    • R13 is selected from the group consisting of H, F, Cl, CF3 and CH3;
    • R14 is H or F; and
    • R15 is selected from the group consisting of H and CH3.


In an embodiment of the invention and/or embodiments thereof,

    • R1 is H;
    • R2 is selected from the group consisting of H, F, and Cl;
    • R3 is selected from the group consisting of H, Cl, F, and Br;
    • R4 is H, F, Cl;
    • R5 is selected from the group consisting of H F, and Cl;
    • R6 is selected from the group consisting of H, F, and Cl, and CH3;
    • R7 is selected from the group consisting of H F, and Cl;
    • R8 is selected from the group consisting of H, F, Cl, and CH3;
    • R9 is selected from the group consisting of H F, and Cl;
    • R11 is H;
    • R12 is selected from the group consisting H, F and Cl;
    • R13 is selected from the group consisting of H, F, and Cl;
    • R14 is H;
    • R15 is selected from the group consisting of H and CH3.


In an embodiment of the invention and/or embodiments thereof,

    • R1 is H;
    • R2 is selected from the group consisting of H, F, and Cl;
    • R3 is selected from the group consisting of H, Cl, F, and Br;
    • R4 is H, F, Cl;
    • R5 is selected from the group consisting of H F, and Cl;
    • R6 is selected from the group consisting of H, F, and CH3;
    • R7 is selected from the group consisting of H F, and Cl;
    • R8 is selected from the group consisting of H, F, and CH3;
    • R9 is selected from the group consisting of H F, and Cl;
    • R11 is H;
    • R12 is selected from the group consisting H, and F;
    • R13 is selected from the group consisting of F and Cl;
    • R14 is H;
    • R15 is selected from the group consisting of H and CH3.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R6, R7, R8, R9, is F.


In an embodiment of the invention and/or embodiments thereof, at least two of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, at least two of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.


In an embodiment of the invention and/or embodiments thereof, at least two of R5, R6, R7, R8, R9, is F.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R6, R7 is a substituent selected from the group consisting of F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R6, R7 is a substituent selected from the group consisting of F, and Cl.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R6, R7 is F.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R7 is a substituent selected from the group consisting of F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R7 is a substituent selected from the group consisting of F, and Cl.


In an embodiment of the invention and/or embodiments thereof, at least one of R5, R7 is F.


In an embodiment of the invention and/or embodiments thereof, R5 and R7 are each a substituent selected from the group consisting of F, Cl, and Br.


In an embodiment of the invention and/or embodiments thereof, R5 and R7 are each a substituent selected from the group consisting of F, and Cl.


In an embodiment of the invention and/or embodiments thereof, R5 and R7 are each F.


In an embodiment of the invention and/or embodiments thereof, 0, 1 or 2 of A1, A2, A3, A4, A5 is N


In an embodiment of the invention and/or embodiments thereof, the compound is a prodrug and at least one of A1, A2, A3, A4, A5 is N═O.


In an embodiment of the invention and/or embodiments thereof, 0, 1 or 2 of A1, A2, A3, A4, A5 is N═O


In an embodiment of the invention and/or embodiments thereof,

    • A1 is CR5 or N;
    • A2 is CR6 or N;
    • A3 is CR7 or N;
    • A4 is CR8 or N;
    • A5 is CR9 or N;
    • wherein no more than 3 of A1, A2, A3, A4, A5 are N.


In an embodiment of the invention and/or embodiments thereof,

    • A1 is CR5 or N;
    • A2 is CR6 or N;
    • A3 is CR7 or N;
    • A4 is CR8 or N;
    • A5 is CR9 or N;
    • wherein 0 or 1 of A1, A2, A3, A4, A5 are N.


In an embodiment of the invention and/or embodiments thereof,

    • A1 is CR5 or N;
    • A2 is CR6 or N
    • A3 is CR7;
    • A4 is CR8;
    • A5 is CR9;
    • wherein 0 or 1 of A1, or A2 are N.


In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (II)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof, wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I, wherein R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, A1, A2, A3, A4, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (II)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof, wherein

    • A2 is CR5, N═O, or N;

    • A2 is CR7, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (II)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof, wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N,

    • A2 is CR6, N═O, or N

    • A3 is CR7, N═O, or N

    • A4 is CR8, N═O or N

    • A5 is CR9, N═O or N

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (II)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR9 or N;

    • A5 is CR9 or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (II)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (II)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (III)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2, R3, R4, R5, R6, R7, R8, R9, R13, R14, R15, A1, A2, A3, A4, and A5 are defined as elsewhere in this description,

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (III)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (III)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N,

    • A2 is CR6, N═O, or N

    • A3 is CR7, N═O, or N

    • A4 is CR8, N═O or N

    • A5 is CR9, N═O or N

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (III)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (III)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (III)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R14, A1, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,

    • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C5)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy; R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N,

    • A2 is CR6, N═O, or N

    • A3 is CR7, N═O, or N

    • A4 is CR8, N═O or N

    • A5 is CR9, N═O or N

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C1-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (V)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R15, A1, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (V)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (V)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (V)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (V)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (V)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R7, R8, R9, R13, A1, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R9 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 3 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • wherein R2, R3, R4, R12, R13, R14, R15, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF31.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • wherein R2, R3, R4, R12, R13, R14, and R15, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (VIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2, R3, R4, R12, R13, R14, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (IX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (X)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (X)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (X)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (X)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (X)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (X)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A2 are N;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, A1, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C5)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C5)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R13, R14, R15, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R13, R14, R15, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R13, R14, R15, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R13, R14, R15, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R13, R14, R15, A1, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C5)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R12, R13, R14, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C5)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, R14, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, R14, A1, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • wherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R12, R13, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C5)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R12, R13, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R12, R1, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 s selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R12 is H;

    • RH is Cl;

    • RH is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, R15, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, R14, R15, A1, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C1-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R13, A2, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of 2 A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • wherein at least one of R6, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R7, R8, R9, R13, A1, A3, A4, and A5 are defined as elsewhere in this description and wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, and Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A3, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R13 is Cl or F;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • wherein at least one of R5, R7, R8, R9, is a substituent selected from the group consisting of F, and Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R13, R14, R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R8, R9, R13, R14, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, R13, R14, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R8, R9, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, R15, A1, A2, A3, A4, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R8, R9, R12, R13, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XL)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, R12, R13, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XL)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XL)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XL)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XL)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XL)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 s selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, CN, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R8, R9, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R7, R8, R9, R12, R13, R14, R15, A2, A3, A4, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • As is CR9, N═O or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A3 is CR7, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A3, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, and —O—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, and CN;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, and (C1-C6)haloalkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, and Cl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A3 is CR7 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A3, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R7 is selected from the group consisting of H, F, and Cl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • or R7 and R8 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, and —NH—, wherein the ring formed by R7 and R8 is optionally substituted with one or more substituents of selected from the group consisting of CH3, F, and Cl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A3 is CR7;

    • A4 is CR8;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, and F;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R8, R9, R12, R13, R14, R15, A1, A2, A4, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A4, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A4, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A4 is CR8;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, R12, R13, R14, R15, A2, A4, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A4, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A4 is CR8, N═O or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A4, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A4 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A4, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A4 is CR8;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLVIIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XLIXa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (L)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (La)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIVa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIVb)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LVIIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIIIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIV)

    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.




embedded image


In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIVa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In a particular embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIa)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R12, R13, R14, and R15, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein,

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R13, R14, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R12, R13, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, R12, R13, R14, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R7 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R8, R9, R13, R14, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C5)alkyl, (C2-C5)alkenyl, (C2-C5)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl;

    • R14 is H;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R8, R9, R12, R13, and R14 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R14 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R14 is selected from the group consisting of H and F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R14 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R8, R9, R12, R13, and R15 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy(C1-C6)alkyl, C(═O)(C1-C6)alkyl, and (C1-C6)alkoxyC(═O)(C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, CH3, and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R12 is H or F;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R12 is H;

    • R13 is Cl;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R8, R9, and R13 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • or R6 and R7 together with the atoms to which they are attached form a 5 or 6-atoms containing ring, wherein the ring-forming atoms are selected from the group consisting of —CH2—, —CH═, ═CH—, —N═, ═N—, —NH—, —O—, —S(O)—, —S(O)2— and —S—, wherein the ring formed by R6 and R7 is optionally substituted with one or more substituents of selected from the group consisting of (C1-C3)alkyl, F, Cl, Br, I, CN, NO2, and ═O;

    • R8 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2, and triazolyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R8 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R8 is selected from the group consisting of H, and F;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R5, R6, R9, R13, R15, A1, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R5, R6, R9, R13, R15, A1, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, As are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, As are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R6, R9, R13, R15, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • A2 is CR6 or N;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R4, R5, R6, R9, R13, R15, A1, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, As are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R4, R6, R9, R13, R15, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R4, R5, R6, R13, R15, A1, and A2, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • wherein no more than 2 of A1, A2, are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • wherein no more than 2 of A1, A2, are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • wherein no more than 2 of A1, A2, are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • wherein 0 or 1 of A1, A2, are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R4, R6, R13, R15, and A2 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R4, R5, R13, R15, and A, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C1-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R4, R6, R9, R13, R15, A1, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXV)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R5, R6, R9, R13, R15, A1, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, As are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R5, R9, R13, R15, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • A2 is CR6 or N;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R2, R3, R4, R6, R9, R13, R15, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A2, A5 are N or N═O;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A2, A5 are N;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXVIII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R2 is selected from the group consisting of H, F, Cl, Br;

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A2 is CR6 or N;

    • A5 is CR9;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R4, R5, R6, R9, R13, R15, A1, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, As are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (LXXXIX)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XC)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R4, R5, R6, R9, R15, A1, A2, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XC)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XC)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A2, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XC)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XC)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A2, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XC)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • A5 is CR9;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R5, R6, R13, R15, A1, and A2, are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • wherein no more than 2 of A1, A2, are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A2 is CR6, N═O, or N;

    • wherein no more than 2 of A1, A2, are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • wherein no more than 2 of A1, A2, are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R6 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, (C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • wherein 0 or 1 of A1, A2, are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, NH(C1-C6)alkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCI)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • A1 is CR5 or N;

    • A2 is CR6 or N;

    • wherein 0 or 1 of A1, or A2 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R6 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein R3, R4, R6, R9, R13, R15, A1, and A5 are defined as elsewhere in this description.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • A1 is CR5, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, As are N or N═O;

    • R3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2 and S-(Halo)5;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, NH2, ═O, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(═NO(C1-C6)alkyl), C(═NO(C1-C6)alkyl)(C1-C6)alkyl, C(═O)(C1-C6)alkyl, C(═O)NH(C1-C6)alkyl, C(═O)NHphenyl, C(═O)O(C1-C6)alkyl, CH(═NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(═O)(C1-C6)haloalkyl), N((C1-C6)alkyl)(C(═O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(═O)O(C1-C6)alkyl)2, N═CH-phenyl, NH((C1-C6)alkylC(═O)(C1-C6)alkyl), NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, NH(C1-C6)alkyl, NH(C1-C6)alkenyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH—C(═O)O(C1-C6)alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(═NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
      • wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)alkyl, NH(C3-C6)cycloalkylCH2O(C1-C6)haloalkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(═O)O—(C1-C6)alkyl;

    • R10 is selected from the group consisting of H, (C1-C6)alkyl, C3-C6)cycloalkyl), (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, C1-C6)alkyloxy-(C2-C6)-alkenyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, heterocycle, aryl and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)haloalkyl;

    • R15 is selected from the group consisting of H, (C1-C6)alkyl.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy;

    • A1 is CR5, N═O, or N;

    • A5 is CR9, N═O or N;

    • wherein no more than 2 of A1, A5 are N or N═O;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH2, ═O, NH(C1-C6)alkyl, N((C1-C6)alky)2, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, N(C1-C6)alkyl-C(═O)|R10, C(═O)(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, and C(═O)—O—(C1-C6)alkyl;

    • R10 is selected from the group consisting H, (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, ((C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, thianyl, phenyl, and (C1-C6)alkylphenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, I, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, and (C2-C6)haloalkenyl;

    • A1 is CR5 or N;

    • A5 is CR9 or N;

    • wherein no more than 2 of A1, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO2, NH(C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, NHC(═O)R10, and N(C1-C6)alkyl-C(═O)|R10;

    • R9 is selected from the group consisting of H, F, Cl, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is selected from the group consisting of H, F, Cl, CH3 and CF3;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6)haloalkyl, and (C1-C6) haloalkoxy;

    • R4 is selected from the group consisting of H, F, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl;

    • A1 is CR8 or N;

    • A5 is CR9 or N;

    • wherein 0 or 1 of A1, A5 are N;

    • R5 is selected from the group consisting of H, F, Cl, CN, NO2, NH(C1-C6)alkyl, and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H, F, and NH(C1-C6)alkyl;

    • R10 is selected from the group consisting (C1-C6)alkyl, (C1-C6)alkyloxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy-(C1-C6)haloalkyl, (C1-C6)alkyl-(C3-C6)cycloalkyl, tetrahydrofuranyl, and phenyl;

    • R13 is Cl or F;

    • R15 is selected from the group consisting of H, and CH3.





In an embodiment of the invention and/or embodiments thereof, the invention is directed to a compound of formula (XCII)




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof,

    • wherein

    • R3 is selected from the group consisting of H, F, Cl, Br, and I;

    • R4 is selected from the group consisting of H, F, Cl, Br;

    • A1 is CR5 or N;

    • A5 is CR9;

    • R5 is selected from the group consisting of H, F, Cl, CN and (C1-C6)alkyl;

    • R9 is selected from the group consisting of H and F;

    • R13 is Cl or F;

    • R15 is H.





In an embodiment of the invention and/or embodiments thereof, the parasitic infestation is an ectoparasite infestation.


In an embodiment of the invention and/or embodiments thereof, the parasitic infestation is a tick infestation and/or flea infestation, preferably a tick infestation.


In an embodiment of the invention and/or embodiments thereof, the parasite is a one host tick.


In an embodiment of the invention and/or embodiments thereof, the parasite is Rhipicephalus microplus.


In an embodiment of the invention and/or embodiments thereof, the parasite is a multi-host tick.


In an embodiment of the invention and/or embodiments thereof, the parasite is an acarid parasite.


In an embodiment of the invention and/or embodiments thereof, the animal is a warm-blooded animal, especially a mammal.


In an embodiment of the invention and/or embodiments thereof, the animal is a livestock animal, especially a bovine animal, especially ruminant, especially cattle.


In an embodiment of the invention and/or embodiments thereof, the animal is a fish, and the parasitic infestation is a sea lice infestation.


In an embodiment of the invention and/or embodiments thereof, the animal is a companion animal, especially canine animal or a feline animal, especially a dog or cat.


In one embodiment the compound of the invention and/or embodiments thereof effectively treats exist and protects Suitably the compounds of the invention and/or embodiments thereof are used in a method, wherein the parasitic infestation is a tick infestation or flea infestation. The compounds are suitably used for a tick infestation.


The compounds of the invention and/or embodiments thereof are suitably used against parasites wherein the parasite is a one host tick or a multi-host tick. Suitably the compounds of the invention are used against Rhipicephalus microplus.


In a suitable use or method of the invention and/or any embodiment thereof, the animal is a warm-blooded animal such as a mammal. However, the compounds of the invention and/or embodiments thereof are also active in a livestock animal, such as a ruminant, bovine animal, or cattle. It was also found that the compounds of the invention and/or embodiments thereof are active in fish, against a sea lice infestation. Also, the compounds of the invention and/or embodiments thereof are found active in a companion animal, such as a canine animal or a feline animal, especially a dog or cat.


Salts, Solvates, N-Oxides and Prodrugs

A salt of the compounds of the Formula (I), or another compound may be advantageous due to one or more of the salt's physical properties, such as pharmaceutical stability in differing temperatures and humidities; crystalline properties; and/or a desirable solubility in water, oil, or other solvent. In some instances, a salt may be used as an aid in the isolation, purification, and/or resolution of the compound. Acid and base salts can typically be formed by, for example, mixing the compound with an acid or base, respectively, using various known methods in the art. To the extent a salt of the compound is intended to be administered in vivo (i.e., to an animal) for a therapeutic benefit, the salt is pharmaceutically acceptable.


Salts may also be of advantage in the synthesis of the compounds according to this invention and/or embodiments thereof. For instance, certain intermediates may advantageously be used in form of their salts in the preparation process of the compounds according to this invention and/or embodiments thereof.


In general, an acid addition salt can be prepared by reacting a free base compound with an approximately stoichiometric amount of an inorganic or organic acid. Non-limiting examples of often suitable inorganic acids for making (pharmaceutically acceptable) salts include hydrochloric, hydrobromic, hydroiodic, nitric, carbonic, sulfuric, and phosphoric acid. Non-limiting examples of often suitable organic acids for making (pharmaceutically acceptable) salts generally include, for example, aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic, carboxylic, and sulfonic classes of organic acids. Specific examples of often suitable organic acids include cholic, sorbic, lauric, acetic, trifluoroacetic, formic, propionic, succinic, glycolic, gluconic, digluconic, lactic, malic, tartaric acid, citric, ascorbic, glucuronic, maleic, fumaric, pyruvic, aspartic, glutamic, aryl carboxylic acid (e.g., benzoic), anthranilic acid, mesylic, stearic, salicylic, p-hydroxybenzoic, phenylacetic, mandelic, embonic (pamoic), alkylsulfonic (e.g., ethanesulfonic), arylsulfonic (e.g., benzenesulfonic), pantothenic, 2-hydroxyethanesulfonic, sulfanilic, cyclohexylaminosulfonic, β-hydroxybutyric, galactaric, galacturonic, adipic, alginic, butyric, camphoric, camphorsulfonic, cyclopentanepropionic, dodecylsulfic, glycoheptanoic, glycerophosphic, heptanoic, hexanoic, nicotinic, 2-naphthalesulfonic, oxalic, palmoic, pectinic, 3-phenylpropionic, picric, pivalic, thiocyanic, tosylic, and undecanoic acid. In some such embodiments, for example, the salt comprises a trifluoroacetate, mesylate, or tosylate salt. In other embodiments, the salt comprises a hydrochloric acid salt.


By way of a non-limiting example, an amine function can form salts with hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric, lactic, gluconic, ascorbic, maleic, aspartic, benzenesulfonic, methanesulfonic, ethanesulfonic, hydroxyl-methanesulfonic, and hydroxyethanesulfonic acids. Additionally, by way of a non-limiting example, an acid function can form salts including those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Examples of preferred cations include sodium, potassium, and magnesium.


In general, a base addition salt can be prepared by reacting a free acid compound with an approximately stoichiometric amount of an inorganic or organic base. Examples of base addition salts may include, for example, metallic salts and organic salts. Metallic salts, for example, include alkali metal (group Ia) salts, alkaline earth metal (group IIa) salts, and other physiologically acceptable metal salts. Such salts may be made from aluminum, calcium, lithium, magnesium, potassium, sodium, and zinc. For example, a free acid compound may be mixed with sodium hydroxide to form such a base addition salt. Organic salts may be made from amines, such as trimethylamine, diethylamine, N, N′-dibenzylethylenediamine, chloroprocaine, ethanolamine, diethanolamine, ethylenediamine, meglumine (N-methylglucamine), and procaine. Basic nitrogen-containing groups may be quaternized with agents such as C1-C6-alkyl halides (e.g., methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides), dialkyl sulfates (e.g., dimethyl, diethyl, dibuytl, and diamyl sulfates), long chain halides (e.g., decyl, lauryl, myristyl, and stearyl chlorides, bromides, and iodides), arylalkyl halides (e.g., benzyl and phenethyl bromides), and others.


Compounds of Formula (I) may be formulated into stable complexes with a solvent, such that the complex remains intact after the non-complexed solvent is removed. These complexes are often referred to as “solvates.” However, it is particularly desirable to form stable hydrates with water as the solvent.


A solvate of a compound of the Formula (I), or another compound may be formed by aggregation of said compound of the Formula (I) with solvent molecules such as water, alcohols, for example ethanol, aromatic solvents such as toluene, ethers, halogenated organic solvents such as dichloromethane, preferably in a definite proportion by weight.


Compounds of Formula (I) containing an acid functionality may be made into ester derivatives. These ester derivatives can then be applied in the same manner as the compounds disclosed in this document are applied.


Compounds of Formula (I) may be made as various crystal polymorphs. Polymorphism is important in the development of veterinary products since different crystal polymorphs or structures of the same molecule can have vastly different physical properties and biological performances.


An N-oxide of a compound of the Formula (I), or another compound may be formed by oxidation of an N-atom in an amine or N-heterocycle such as pyridine and pyrimidine by oxidation agents such as hydrogen peroxide, peracids or inorganic oxidation agents such as potassium peroxymonosulfate (oxone).


This invention also encompasses prodrug derivatives of the compounds of Formula (I). The term prodrug refers to compounds that are transformed to yield the parent compound of Formula (I). Transformation often occurs in vivo. In vivo means that in the case of, for example, treatment of a parasitic infestation this transformation can occur in the host organism and/or the parasite. Various forms of prodrugs are well known in the art. For example, if the group of Formula (I) represents a pyridine, it is possible to form pyridinium salts such as, for example, acyloxyalkylpyridinium salts, which can offer advantages in terms of higher solubility for parenteral dosage forms, which are described in S. K. Davidsen et al., J. of Med. Chem. 37 4423-4429 (1994).


Compounds of Formula (I) may be made with different isotopes. Of particular importance are molecules having 2H (also known as deuterium) or 3H (also known as tritium) in place of 1H. Molecules of Formula One may be made with different radionuclides. Of particular importance are molecules having 14C (also known as radiocarbon). Molecules of Formula (I) having deuterium, tritium, or 14C may be used in biological studies allowing tracing in chemical and physiological processes and half-life studies, as well as MoA studies.


Isomers

The compounds of Formula (I) may exist in different geometric or optical isomeric or different tautomeric forms. One or more centers of chirality may be present in which case compounds of Formula (I) may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers. It will be appreciated by those skilled in the art that one stereoisomer may be more active than the other stereoisomers. Individual stereoisomers may be obtained by known selective synthetic procedures, by conventional synthetic procedures using resolved starting materials, or by conventional resolution procedures. There may be double bonds present in the molecule, in which case compounds of Formula (I) may exist as single geometric isomers (cis or trans, E or Z) or mixtures of geometric isomers (cis and trans, E and Z). Centers of tautomerisation may be present. This disclosure covers all such isomers, tautomers, and mixtures thereof, in all proportions. In some embodiments, such compounds may have two or more isomers, such as optical isomers or conformational isomers. For example, the compounds can have a (E) or (Z) configuration at the —CXR3═CR1R2 double bond, such as in alkenyl or alkynyl substituents of the ring formed by A1 to A5. In some preferred embodiments, such compound has the (E) configuration, in other embodiments, the compound has the (Z) configuration. In a preferred embodiment the compounds have (E) configuration.


Unless otherwise stated, a compound structure that does not indicate a particular conformation is intended to encompass all the possible conformational isomers of the compound, as well as comprising fewer than all the possible conformational isomers. Compounds with two chiral centers have four isomers: the RR-, SS-, RS-, and SR-isomers. Such compounds may exist in a number of forms i.e., in the pure RR or SS or RS or SR isomeric forms, or as mixtures, hereinafter called “enantiomeric pairs” of either RR/SS or RS/SR. The compound ***can also exist as racemic mixtures of all four isomers (RR+SS+RS+SR) or in the form of racemic mixtures of the enantiomeric pairs (RR/SS) or (RS/SR). The isomers (RR) and (SS) are mirror images of each other and are therefore enantiomers, which have the same chemical properties and melting points. (RS) and (SR) is similarly an enantiomeric pair. The mirror images of (RR) and (SS) are not, however, super imposable on (RS) and (SR). This relationship is called diastereomerism, and (RR) is a diastereomer to (RS).


Although structurally identical, isomers can have different effects in biological systems: one isomer may have specific therapeutic activity while another isomer may have no therapeutic activity or may have entirely different forms of biological activity.


In the compounds of the invention, the cyclopropane contains 2 chiral centers, one bonded to the phenyl and the other bonded to the carboxamide group.


It has now surprisingly been found that parameters, such as for example efficacy can be greatly improved by administering pure or substantially pure RR-isomer of compounds according to the invention and embodiments as described herein, a pharmaceutically acceptable salt, thereof, while side effects can be substantially avoided. Thus, the applicant has found that by administering a therapeutically effective amount of the pure or substantially pure RR-isomer of compounds according to the invention and embodiments as described in any embodiment, a pharmaceutically acceptable salt, thereof.


Terms like “pure RR-compounds according to the invention and embodiments as described in any embodiment”, “pure RR-isomer of compounds according to the invention and embodiments as described in any embodiment” and the like, refer to compounds according to the invention and embodiments as described in any embodiment having an optical purity of RR-compounds according to the invention and embodiments as described in any embodiment that is 98% by weight or better, which means the RR-isomer is present at a concentration of 98% by weight or more, while the total concentration (i.e. the sum) of the corresponding RS-, SR- and SS-isomers is 2% by weight or less, based on the total amount of compounds according to the invention and embodiments as described in any embodiment present.


The terms “substantially pure RR-compounds according to the invention and embodiments as described in any embodiment”, “substantially pure RR-isomer of compounds according to the invention and embodiments as described in any embodiment” and the like, refer to an optical purity of RR-compounds according to the invention and embodiments as described in any embodiment that is 80% by weight or better which means a concentration of 80% weight or more of RR-compounds according to the invention and embodiments as described in any embodiment and 20% by weight or less of the sum of the corresponding RS-, SR- and SS-isomers, based on the total amount of compounds according to the invention and embodiments as described in any embodiment present. In a more preferred embodiment, a “substantially pure RR-compounds according to the invention and embodiments as described in any embodiment” contains 90% by weight or more of RR-compounds according to the invention and embodiments as described in any embodiment and 10% or less of the sum of the RS and SR and SS-isomers of compounds according to the invention and embodiments as described in any embodiment.


In a suitable embodiment the compounds of Formula (I), the carboxamido, and the phenyl, which are bonded to the cyclopropane, are in the R,R configuration. This embodiment may be used in combination with any of the other embodiments of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, and R15.


In an embodiment of the invention and/or embodiments thereof, the parasitic infestation is an ectoparasite infestation.


In an embodiment of the invention and/or embodiments thereof, the parasitic infestation is a tick infestation or flea infestation, preferably a tick infestation.


In an embodiment of the invention and/or embodiments thereof, the parasite is a one host tick.


In an embodiment of the invention and/or embodiments thereof, the parasite is Rhipicephalus microplus.


In an embodiment of the invention and/or embodiments thereof, the parasite is a multi-host tick.


In an embodiment of the invention and/or embodiments thereof, the parasite is an acarid parasite.


In an embodiment of the invention and/or embodiments thereof, the animal is a warm-blooded animal, especially a mammal.


In an embodiment of the invention and/or embodiments thereof, the animal is a livestock animal, especially a bovine animal, especially ruminant, especially cattle.


In an embodiment of the invention and/or embodiments thereof, the animal is a fish, and the parasitic infestation is a sea lice infestation.


In an embodiment of the invention and/or embodiments thereof, the animal is a companion animal, especially canine animal or a feline animal, especially a dog or cat.


In an embodiment of the invention and/or embodiments thereof, the animal is protected from a parasite infestation.


In an embodiment of the invention and/or embodiments thereof, an existing parasite infestation of the animal is treated or controlled.


In an embodiment of the invention and/or embodiments thereof, the method comprises administering the compound to an animal weekly, bi-weekly, monthly, every 6 weeks, every 2 months or every 3 months.


In an embodiment of the invention and/or embodiments thereof, the parasite infestation of the animal is prevented for at least one week.


The present invention is also directed to a veterinary composition comprising an effective amount of a compound of Formula (I) as defined in any embodiment described herein and an inert carrier or formulation adjuvant. Suitably the composition is used in the treatment and control of a parasitic infestation of animals as described herein.


In an embodiment of the invention and/or embodiments thereof, the veterinary composition is a topical composition.


In an embodiment of the invention and/or embodiments thereof, the veterinary composition is an oral composition.


In an embodiment of the invention and/or embodiments thereof, the veterinary composition is an injection composition.


Methods According to this Invention

The compounds of the invention and/or embodiments thereof as described in this application and were applicable, pharmaceutically acceptable solvates, N-oxides, salts and prodrugs thereof may generally be used as a medicament for animals wherein one or more, preferably one compound according to this invention and/or embodiments thereof is administered to an animal in order to treat, or control parasitic infestations.


Suitably the compounds of the invention and any embodiments thereof are for use in a method of treatment or control of a parasitic infestation of an animal.


Another aspect of the current invention are compositions, comprising such compounds and veterinary or pharmaceutically acceptable excipients for use in treatment and/or protection animals from parasite infestation.


An “infestation” refers to the presence of parasites in numbers that pose a risk of nuisance or harm to animals. The presence can be in the environment, on the skin or fur of an animal or in the animal's blood, organs or tissues, etc.


The term “(parasitic) infestation” includes conditions associated with or caused by one or more (parasitic) pathogens; said conditions include clinical conditions (parasitoses) and sub-clinical conditions.


The term “treatment of parasitic infestation” thus includes both the treatment of parasitoses and the treatment of sub-clinical conditions. The treatment of a parasite infestation generally implies the suppression of parasite burden of the animal below that level at which economic loss occurs. Treating (parasitic) infestations” means to partially or completely inhibit the development of (parasitic) infestations of an animal susceptible to (parasitic) infestation, reduce or completely eliminate the symptoms of infestations of an animal having infestations, and/or partially or completely cure infestations of an animal having infestations. This can be achieved by alleviating or reducing pathogen numbers such as parasite numbers in or on an animal.


Sub-clinical conditions are typically conditions not directly leading to clinical symptoms in the parasite infested animal but leading to economic losses. Such economic losses can be e.g., by depression of growth in young animals, lower feed efficiency, lower weight gain in meat producing animals, lower milk production in ruminants, or lower wool-production in sheep.


The term ‘treatment,’ and similar terms such as ‘treating’ or ‘treat’ as used herein, refer to the administration of an effective amount of at least one compound as described for use in the invention to an animal which has an infestation—of more or less severity—with parasites of one or more species The term “control” as used herein with regard to the field of animal health means that the compounds act by reducing the occurrence of the parasite in question in or on an animal, that is infested or is at risk to be infested with such parasites, to a harmless level. The control of parasites is a medical care given to animals that are infested or are at risk to be infested with such parasites. T This means to to reduce or eradicate parasite numbers in and/or on an animal, and/or to partially or completely inhibit the development of parasite infestation in and/or on an animal. This may be achieved by, for example, killing, repelling, expelling, incapacitating, deterring, eliminating, alleviating parasites, or minimizing the parasite infestation.


Therefore, control refers to either ameliorating or eliminating a current parasitic infestation, and/or preventing or diminishing a future infestation or a re-infestation of an animal or an animal population.


Within the context of the invention, the term ‘control’ includes, particularly, the preventive treatment of animals against a parasite infestation/infection. The preventive treatment of an animal against a disease or condition designates a treatment made before the animal has been exposed to or in contact with the causative agent of the disease or condition (e.g., a parasite especially infectious stages of parasites) or after said exposure/contact but before development of the detrimental conditions (e.g. before sub-clinical conditions, such as production losses in livestock appear, (e.g. reduction of milk production, reduced weight gain, wool loss), before appearance of clinical symptoms or at an early stage of development of the disease.


More specifically, “control” as used herein means that the compound kills the parasite in question, retards its growth or inhibits its proliferation.


The effect can be e.g., ovicidal, larvicidal and/or adulticidal or a combination thereof. The effect can manifest itself directly, i.e., killing the parasites either immediately or after some time has elapsed, for example when molting occurs, or by destroying their eggs, or indirectly, e.g., reducing the number of eggs laid and/or the hatching rate.


Therefore, control refers to either ameliorating or eliminating a current parasitic infestation, and/or preventing or diminishing a future infestation or a re-infestation of an animal or an animal population.


Control of the parasites can also contribute to preventing the transmission of infectious agents to animals by parasite (vector control). The compounds of the Formula (I) can also be used in vector control. In the context of the present invention, a vector is especially an arthropod, especially an insect or arachnid or crustacean, capable of transmitting pathogens, for example, viruses, worms, single-cell organisms, and bacteria, from a reservoir (plant, animal, human, etc.) to a host animal.


An example of vectors and the diseases or pathogens they transmit are ticks, that transmit tick-borne encephalitis, Q fever (Coxiella burnetii), borreliosis (Lyme disease caused by Borrelia spp. e.g., Borrelia burgdorferi), babesiosis (or piroplasmosis caused by Babesia spp.) and rickettsioses (e.g., Rocky Mountain spotted fever).


The term “parasitoses” relates to clinically manifest pathologic conditions and diseases associated with or caused by an infestation by one or more parasites directly, such as, for example, anemia and flea allergy dermatitis. It also includes pathologic conditions or diseases associated with caused by one or more vector-transmitted pathogens, such as, for example, Lyme disease, ehrlichiosis (particularly canine ehrlichiosis), and Rocky Mountain spotted fever from vector ticks.


The phrase “treatment of parasitoses” means to partially or completely inhibit the development of parasitoses of an animal, reduce or completely eliminate the symptoms of parasitoses of an animal, and/or partially or completely cure parasitoses of an animal.


In general, the control of parasitic infestation including parasitoses is achieved by administering an effective amount of one or more, preferably one compound according to this invention.


The terms “prevent”, “prevention” or “prophylaxis” are intended to mean the administration of the compounds of the present invention to the animal before the parasitic infection or infestation has occurred in order to keep said infection or infestation from occurring. Administration of the compound at recommended regular intervals effectively prevents new parasitic infestations or infections in animals by killing new parasites that attack an animal before they can multiply to establish an infestation or infection.


Also, the term ‘preventive treatment’, in relation to a population of animals, designates the treatment of all members of the population even after the disease or condition (e.g., parasite infestation) has been detected in only certain animals, to limit or avoid spreading of and contamination to the other members of the animal population.


The compounds according to the present invention act against animal parasites, in particular ectoparasites and/or endoparasites. Ectoparasites are parasites that live on the external surface of host animals. Endoparasites are parasites that live in the internal organs or tissues of its host.


Ectoparasites are parasites that live on the external surface of host animals.


Endoparasites are parasites that live in the internal organs or tissues of its host.


Ectoparasites are typically and preferably arthropods, especially insects such as flies (biting and licking), parasitic fly larvae, lice, fleas, and the like; or acarids such as ticks, for example hard ticks or soft ticks, or mites such as scab mites, mange mites or demodex mites and the like. Important ectoparasites of fish are crustacean parasites such as aquatic ectoparasites such as sea lice.


Ectoparasites tend to irritate the animals and can also cause clinical disease and adverse sub-clinical conditions, either by themselves or by carrying vector-transmitted pathogens.


Specifically, ticks parasitize on wild as well as domesticated animals, and are known to be responsible for the transmission of pathogens including bacteria, viruses, and protozoan parasites. Ticks also release toxins which cause inflammation or paralysis in the host. Occasionally, these toxins are fatal to the host.


On the other hand, such ectoparasites seriously impact productivity in the livestock animal industry by reducing weight gain, or milk production, causing inferior quality hide, wool, and meat, and in some cases resulting in mortality. Ectoparasites are also responsible, in part, for the spread of pathogens as vectors and cause discomfort in livestock and companion animals impacting animal welfare.


In one embodiment of the invention and/or embodiments thereof, the ectoparasite is selected from the group consisting of flies, parasitic fly larvae, lice, fleas, ticks, mites, and sea lice.


In one embodiment of the invention and/or embodiments thereof, the ectoparasite is an insect or an acarid. Suitably the insect is not a mosquito. Suitably the ectoparasite is an acarid.


Suitably the acarid ectoparasite is a hard tick, soft tick, or mite.


Suitably the ectoparasite is a sea lice.


For example, a parasite which is prevalent among livestock animals, such as cattle, is the tick of the genus Rhipicephalus, especially those of the species R. microplus (tropical cattle tick), R. decoloratus and R. annulatus. Ticks such as Rhipicephalus microplus (formerly Boophilus microplus) are difficult to control.


This species of ticks is considered a one-host tick and lives as immature and adult stages on one animal before the female engorges and falls off the host to lay eggs in the environment. The life cycle of the tick is approximately three to four weeks. In addition to cattle, Rhipicephalus microplus may infest buffalo, horses, donkeys, goats, sheep, deer, pigs, and dogs.


Veterinary relevant ectoparasites of warm-blooded animals (generally insect and acarid pests) include the following:


Insects. These are parasitic stages of flies, fleas, lice, bugs include, for example, migrating diperous larvae, such as, for example, Hypoderma sp. in cattle, Gastrophilus in horses, and Cuterebra spp. in rodents; biting flies, such as, for example, bloodsucking adult flies (e.g., the horn fly (Haematobia irritans), horse flies (Tabanus spp.), stable flies (Stomoxys calcitrans), black flies (Simulium spp.), deer flies (Chrysops spp.), louse flies (Melophagus ovinus), tsetse flies (Glossina spp.); parasitic fly maggots, such as, for example, bot flies (Oestrus ovis and Cuterebra spp.), the blow flies (Phaenicia spp.), screwworms (Cochliomyia hominivorax), cattle grubs (Hypoderma spp.), and fleeceworms; Suitably the insect is not a mosquito.


Lice. These include, for example, chewing lice, such as Menopon spp. and Bovicola spp.; and sucking lice, such as Haematopinus spp., Linognathus spp., and Solenopotes spp.


Fleas. These include, for example, Ctenocephalides spp., such as dog fleas (Ctenocephalides canis) and cat fleas (Ctenocephalides felis); Xenopsylla spp., such as oriental rat fleas (Xenopsylla cheopis); Pulex spp., such as human fleas (Pulex irritans); hedgehog fleas (Archaeopsylla erinacei); and bird fleas (Ceratophyllus gallinae).


True bugs. These include, for example, Cimicidae or the common bed bug (Cimex lectularius); and Triatominae spp., such as triatomid bugs (also known as kissing bugs) (e.g., Rhodnius prolixus and Triatoma spp.).


Mites. These include:

    • i. Mesostigmata spp., such as mesostigmatids, which include chicken mites (Dermanyssus gallinae).
    • ii. Ii. Astigmata spp., such as itch or scab mites, which include Sarcoptidae spp. (e.g., Sarcoptes scabiei); and mange mites, which include Psoroptidae spp. (e.g., Chorioptes bovis and Psoroptes ovis).
    • iii. lii. P rostigmata spp, such as chiggers, which include Trombiculidae spp. (e.g., North American chiggers, Trombicula alfreddugesi).


Iv. Demodex spp.


Ticks. These include, for example, soft-bodied ticks, such as Argasidae spp. (e.g., Argas spp. and Ornithodoros spp.); and hard-bodied ticks, such as Ixodidae spp. (e.g., Ixodes ricinus, Rhipicephalus sanguineus, Haemaphysalis spp, Dermacentor reticulatus, Dermacentor variabilis, Amblyomma americanum, and Rhipicephalus (Boophilus) spp.).


In one embodiment the ectoparasite is a tick from the genera Rhipicephalus (Boophilus), Dermacentor, Ixodes, Ambylomma, Haemaphysalis, Hyalomma especially Rhipicephalus (Boophilus), especially those of the cattle tick species R. microplus, R. decoloratus and R. annulatus.



Rhipicephalus microplus, R. decoloratus and R. annulatus are single host ticks, this means all three stages of the lifecycle live on the same animal.


Multi-host ticks drop to the ground after each stage has fed on an animal and re-attach to another host after molting. The species of host between the distinct stages may differ. Representatives of multi-host ticks are e.g., Amblyomma cajennense, Ixodes holocyclus, i.e., paralysis tick: H. longicornis, Rhipicephalus appendiculatus and Amblyomma hebraeum, Dermacentor albipictus, Amblyomma maculatum, Amblyomma andersoni, Ixodes ricinus, Dermacentor marginatus.


The main reasons for tick control in livestock animals are to protect hosts from irritation and production losses, formation of lesions that can become secondarily infected, damage to hides and udders, toxicosis, paralysis, and of greatest importance, infection with a wide variety of disease agents.


The ectoparasite infestations of animals treated by the compounds include, but are not limited to fleas, ticks, mites, flies, lice, blowfly, and co-infestations with more than one species thereof.


In one preferred embodiment, the compounds of the invention are used for the treatment of or protection of animals from parasitic infections and infestations in companion animals, especially dogs and cat, especially to control infestations with fleas and/or ticks, or mites especially Ctenocephalides felis, Rhipicephalus sanguineus, Ixodes ricinus, Dermacenter variabilis, Amblyomma americanum, Ixodes scapularis, Dermacentor reticulatus, Hyalomma spp. and/or Ixodes holocyclus.


In another preferred embodiment, the compounds of the invention are used for the treatment of or protection from parasitic infections and infestations in dogs and cats, especially to control infestations with Demodex spp. mites.


The compound is suited for the treatment of tick infestations (Dermacentor reticulatus, Ixodes hexagonus, Ixodes ricinus and Rhipicephalus sanguineus) in dogs and/or cats. The compound has immediate and persistent tick killing activity for at least 5 weeks. For the treatment of flea infestations (Ctenocephalides felis and Ctenocephalides canis) the compound has immediate and persistent flea killing activity against new infestations for at least 5 weeks. The compound can be used as part of a treatment strategy for the control of Flea Allergy Dermatitis (FAD). The compound can be used for the treatment of sarcoptic mange (Sarcoptes scabiei). The compound is suited for the treatment of ear mite infestations (Otodectes cynotis). The compound is suited for the treatment of demodicosis (Demodex canis).


The compound is suited to kill adult fleas and is indicated for the treatment and prevention of flea infestations (Ctenocephalides felis) and the treatment and control of Blacklegged tick (Ixodes scapularis), American Dog tick (Dermacentor variabilis), Lone Star tick (Amblyomma americanum), and Brown Dog tick (Rhipicephalus sanguineus) infestations in companion animals, in dogs and/or cats.


In another preferred embodiment, the compounds of the invention are used for the treatment of or protection from parasitic infections and infestations in livestock, especially ruminants such as cattle or sheep. When treating livestock animals such as cattle or sheep, the compounds are particularly effective against Rhipicephalus (Boophilus) microplus, Haematobia irritans (horn fly), Stomoxys calcitrans (stable fly), and myiases such as Lucilia sericata, (European green blowfly), Lucilia cuprina (Green blowfly or Australian sheep blowfly known as blowfly strike in Australia, New Zealand and South Africa), Chrysomya rufifacies (Hairy maggot fly), Chrysomya varipes (Small green blowfly), Calliphora stygia (Common brown blowfly), Calliphora augur (Lesser brown blowfly (eastern), Calliphora novicia (Lesser brown blowfly (western).


Sucking lice consume a blood meal from their host and are more important in transmitting pathogens. Chewing or biting lice ingest fur and skin and sometimes blood from their host; important lice parasites are the cattle biting louse (Bovicola bovis), the longnosed cattle louse (Linognathus vituli), the little blue cattle louse (Solenopotes capillatus), the shortnosed cattle louse (Haematopinus eurysternus), and the cattle tail louse (Haematopinus quadripertusus) and the sheep biting louse of sheep and goats (Bovicola ovis).


In one embodiment the compounds of the invention are used for the treatment of or protection from parasitic infections and infestations by mange mites like Chorioptes bovis, Sarcoptes scabiei and Psoroptes ovis.


The above list is not exhaustive and other ectoparasites are well known in the art to be harmful to animals, especially livestock animals, especially ruminants, more especially cattle or sheep. These include, for example migrating dipterous larvae.


It has been surprisingly found that the compounds or composition of the invention are effective to control one or more of these parasites.


Important ectoparasites of cold-blooded animals like fish are sea lice. Sea lice are ectoparasites which feed on the mucus, epidermal tissue, and blood of host marine fish, in particular salmon. Sea lice belong to the sub-class of copepods. As used herein, the term “sea lice” refers to all members of the family Caligidae; in particular, it includes Lepeophtheirus salmonis, Caligus rogercresseyi, C. elongatus and Caligus clemensi or the family Lernanthropidae; it includes Lernanthropus kroyeri.


Sea lice can cause significant harm to host fish, in particular they can cause serious fin damage, skin erosion, bleeding, and open wounds. Additionally, sea lice can cause chronic stress response in fish, which in turn can make them susceptible to other diseases. Sea lice infestations are a major problem in fish farming and can result in significant economic loss.


The term “endoparasites” includes especially helminths such as cestodes, nematodes or trematodes, and protozoa such as coccidia. Endoparasites include nematode pests which commonly infect animals, and include the egg, larval, and adult stages thereof. Such pests include helminths (roundworms, hookworms, tapeworms, heartworms), and are commercially important because they cause serious diseases in animals.


In some embodiments of the invention, especially in case the compound is combined with another active ingredient, the composition can also be used to treat against endoparasites such as those caused by one or more helminths selected from the group consisting of a) cestodes: e.g., Anaplocephala spp.; Dipylidium spp.; Diphyllobothrium spp.; Echinococcus spp.; Moniezia spp.; Taenia spp.; b) trematodes e.g. Dicrocoelium spp.; Fasciola spp.; Paramphistomum spp.; Schistosoma spp.; or c) nematodes, e.g.; Ancylostoma spp.; Anecator spp.; Ascaridia spp.; Ascaris spp.; Brugia spp.; Bunostomum spp.; Capillaria spp.; Chabertia spp.; Cooperia spp.; Cyathostomum spp.; Cylicocyclus spp.; Cylicodontophorus spp.; Cylicostephanus spp.; Craterostomum spp.; Dictyocaulus spp.; Dipetalonema spp; Dirofilaria spp.; Dracunculus spp.; Enterobius spp.; Filaroides spp.; Habronema spp.; Haemonchus spp.; Heterakis spp.; Hyostrongylus spp.; Metastrongylus spp.; Meullerius spp. Necator spp.; Nematodirus spp.; Nippostrongylus spp.; Oesophagostomum spp.; Onchocerca spp.; Ostertagia spp.; Oxyuris spp.; Parascaris spp.; Stephanurus spp.; Strongylus spp.; Syngamus spp.; Toxocara spp.; Strongyloides spp.; Teladorsagia spp.; Toxascaris spp.; Trichinella spp.; Trichuris spp.; Trichostrongylus spp.; Triodontophorous spp.; Uncinaria spp., and/or Wuchereria spp.


In a suitable use of the invention and/or any embodiment thereof, the animal is protected from a parasite infestation. In one embodiment an existing parasite infestation of the animal is treated or controlled. In another embodiment an existing parasite infestation of the animal is treated or controlled, and the animal is protected from a parasite infestation Another embodiment is a method of protecting animals that are at risk to be infested by parasites comprising administering an effective amount of at least one compound of the invention and/or embodiments thereof to the animals using a single administration.


In one embodiment the invention provides a composition comprising an effective amount of a compound of the invention and/or embodiments thereof when used for the treatment of parasite infestations of animals and/or for the protection of animals from infestation by parasites, wherein the composition is administered to an animal that has been diagnosed or is suspected to be infested by parasites. In one embodiment the composition is administered to an animal that is at risk to be infested by parasites to PROTECT it from such infestation.


In a suitable use of the invention and/or any embodiment thereof, the method comprises administering a compound of the invention and/or embodiments thereof to an animal weekly, bi-weekly, monthly, every 6 weeks, every 2 months, every 3 months, every 4 months, every 6 months, or every 9 months.


Surprisingly a number of compounds of the invention and/or embodiments thereof were also able to protect various species of animals from parasite infestation.


In an embodiment of the invention and/or embodiments thereof, the animal is protected from a parasite infestation.


In an embodiment of the invention and/or embodiments thereof, a ruminant animal, preferably a cattle anima is protected, preferably from an infestation with ticks is. In one embodiment the tick is a one host tick. In another embodiment the tick is a multi-host tick.


In an embodiment of the invention and/or embodiments thereof, a companion animal, preferably dog or cat is protected, preferably from an infestation with ticks and/or fleas, preferably ticks, preferably ticks and fleas.


In an embodiment of the invention and/or embodiments thereof, the method comprises administering the compound to an animal weekly, bi-weekly, monthly, every 6 weeks, every 2 months, every 3 months, every 6 months or every nine months.


Another aspect of the current invention are compositions, comprising compounds of the invention and/or embodiments thereof and veterinary or pharmaceutically acceptable excipients for use in treatment and/or protection of animals from parasite infestation.


“Protection or protect” means that a new infestation or re-infestation of an animal, or a mob or flock or herd with parasites is prevented by killing adult parasites and any development/larval stages, that are able to infest the host, before infestation of the host or, by killing or inhibiting the parasites when they infest an animal that has been treated with a compound or preventng generation of offspring of the parasites e.g. reducing the number of eggs laid and/or the hatching rate.


For use in the invention “protection from re-infestation” covers the situation where the animal is exposed to a new infestation by the parasite because it either lives in an environment were living parasites are present or is in close contact with parasite infested animals (or humans)—is therefore “at risk to be infested.”


Re-infestation is a second or subsequent infestation by parasites. This means an animal that is at a certain point (substantially) free from a parasite infestation is infested (again) with parasites from external sources. The compounds or composition of the invention kills such new emerging parasites before they can establish an infestation of the animal, or alternatively reduce the number of parasites to limit the irritation and damage to the animal by allowing a non-significant number of parasites.


“Protection period” means the time, expressed in days or weeks after the treatment, that a veterinary test product will prevent the ectoparasite re-infestation of the animal hosts. Sometimes referred to as the prophylactic period or the persistent efficacy period (WAAVP guidelines 2006)


Protective periods may be e.g., useful when treated animals contact untreated animals, or when treated and untreated animals become mixed.


The frequency of the administration will be dependent upon several factors and can be a single dose administered once a day, or depending on the protection period once a week, once a month, once every two, three, four, or six months, or nine months, or once every year. In some embodiments, the frequency of administration may be, for example, weekly, bi-weekly, monthly, bi-monthly, every 3 month, every 4 month, every 5 month, every 6 month, every 9 months or every 12 month or the equivalent administration frequency expressed in days or weeks that approximate such frequency.


In one embodiment, the composition comprising a compound of the invention and/or embodiments thereof exhibits long lasting efficacy and provides protection against parasites in animals, especially livestock animals for at least one month.


In another embodiment, compounds of the invention and/or embodiments thereof exhibit very long-lasting efficacy of at least 50% against ticks that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months or at least 5 months, at least 6 months or 9 months.


In another embodiment, the compounds of the invention and/or embodiments thereof exhibit very long-lasting efficacy of at least 70% against ticks that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months or at least 5 months, at least 6 months or 9 months.


In another embodiment, the compounds of the invention and/or embodiments thereof exhibit very long-lasting efficacy of at least 90% against parasites such as e.g., ticks that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months, or at least 5 months, at least 6 months or 9 months.


In another embodiment, the compounds of the invention and/or embodiments thereof exhibit very long-lasting efficacy of at least 90% against parasites such as fleas that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months, or at least 5 months, at least 6 months or 9 months.


In an embodiment of the invention and/or embodiments thereof, the parasite infestation of the animal is prevented for at least one week, preferably at lest 10 days, at least two weeks, 3 weeks, 4 weeks, 6 weeks, 8 weeks, 10 weeks, 12 weeks, 16 weeks, 26 weeks or 36 weeks.


In an embodiment of the invention and/or embodiments thereof, the parasite infestation of the animal is prevented or controlled for at least two weeks, 3 weeks, 4 weeks, 6 weeks, 8 weeks, 10 weeks, 12 weeks, 16 weeks, 26 weeks or 36 weeks.


In an embodiment of the invention and/or embodiments thereof, the parasite infestation of the animal is prevented or controlled for at least one months, 2 months, 3 months, 6 months, or 9 months.


A single administration of a compound of the invention and/or embodiments thereof is typically sufficient to protect animals from a parasitic infestation. Although such a single dose is typically preferred, it is contemplated that multiple doses can be used for a single treatment.


Another embodiment is a method of treating animals that have been diagnosed or are suspected to be infested by parasites comprising administering an effective amount of at least one compound of the invention and/or embodiments thereof to the animals using a single administration.


In an embodiment of the invention and/or embodiments thereof, an existing parasite infestation of the animal is treated or controlled.


In an embodiment of the invention and/or embodiments thereof, an existing parasite infestation of a companion animal, preferably dog or cat, preferably an infestation with ticks and/or fleas, preferably ticks, preferably ticks and fleas is treated.


In an embodiment of the invention and/or embodiments thereof, an existing parasite infestation of a ruminant animal, preferably a cattle animal, preferably an infestation with ticks is treated. In one embodiment the tick is a one host tick. In another embodiment the tick is a multi-host tick.


A single administration of a compound of the invention and/or embodiments thereof is typically sufficient to treat a parasitic infestation. Although such a single dose is typically preferred, it is contemplated that multiple doses can be used for a single treatment.


The compounds according to this invention are useful in a medicament, especially a medicament for treating and controlling such parasitic infestations of animals. In such medicament a concentration of a compound of the invention and/or embodiments thereof is present that is administered as an effective amount to an animal in need thereof.


An “effective amount,” is the amount or quantity of a compound that is required to cause a measurable reduction in the ectoparasite population infesting an animal, and/or to inhibit the development of parasite infestations of an animal, in whole or in part. Alternatively, this may refer to an amount, dose, or quantity that can effectively control and/or reduce presence of parasites in an animal's housing or its surroundings, e.g., the house, building, farm, etc.


This amount is readily determined by observation or detection of the parasite numbers both before and after contacting the animals with the compound. When the compound shows an effect via feeding/ingestion by the parasite, an effective amount generally constitutes an amount that results in tissue and/or blood concentrations generally toxic when ingested by the target parasite.


To establish that an effective reduction of infestation of an animal, or an effective control and/or reduction of parasites in the surroundings has occurred, and thus: what constitutes such an effective amount, is readily determined by comparing the parasite numbers either on the animal or in an animal's environment, before and after administering a compound as described herein.


Detection can be e.g., done by counting of the number of parasites visible on an animal, or by counting parasites using a trap or other detection-device in the surroundings.


The difference in numbers from such counts made before and after treatment indicates the efficacy of the dose applied e.g., the parasite count is reduced, after a first administration, by an amount ranging from 5% to about 100%.


So, although reductions at—or close to 100% are aimed for, however a reduction in parasite numbers of about 50% may already constitute a significant reduction. This because even such a modest reduction already alleviates certain symptoms for affected animals, and/or may restore the animals to an improved economic production level.


In one embodiment, an effective amount of the active agent achieves at least about 80%, or at least about 90% efficacy against the target parasites. In a specific preferred embodiment, the efficacy is at least about 95%.


In a preferred embodiment, the reduction of infestation on an animal, or the control and/or reduction achieved, regards a reduction in the number of a particular type of parasite by at least 50, 60, 70, 75, 80, 85, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or even 100%, in that order of preference. The duration of activity or efficacy (i.e., “knockdown,” onset of activity and/or sustained effects) can be the primary concern in antiparasitic product choices. Products are evaluated based on both their immediate and residual speed of kill and duration of efficacy. A rapid residual speed of kill, sometimes called onset of activity/efficacy is critically important when attempting to reduce the chances of a (tick) parasite transmitting a pathogen. The durations over which the compounds are effective against various ectoparasites is important for the required treatment interval. This is particularly important, especially considering that such long activities are obtained when using low doses that are non-toxic to the target animal.


In another embodiment, the compounds of the invention provide an efficacy against ectoparasites of at least 95.0% or higher for about 3 months or longer.


In other embodiments, the compounds of the invention have an efficacy of at least about 90% against ectoparasites including, but not limited to, fleas, ticks, mites and parasitic flies, of about 7 months or longer, about 8 months or longer or about 9 months or longer.


In other embodiments, the compounds of the invention have an efficacy of at least about 90% against ectoparasites including, but not limited to, fleas, ticks, mites and parasitic flies, of about 10 months or longer, about 11 months or longer or even about 12 months or longer.


Therefore, one embodiment of the invention is a method wherein the compound is administered every month.


Therefore, in another embodiment of the invention the compound is administered every 6 weeks.


Therefore, in another embodiment of the invention the compound is administered every 2 months.


Therefore, in another embodiment of the invention the compound is administered every 10 weeks.


Therefore, in another embodiment of the invention the compound is administered every 3 months.


Therefore, in another embodiment of the invention the compound is administered every 6 months.


Therefore, in another embodiment of the invention the compound is administered every 9 months.


In one embodiment an effective dose of the compound protects animals, especially cattle from infestation or re-infestation by parasites such as e.g., ticks, mites, lice and/or biting flies for at least 48 days.


Therefore, in one embodiment of the invention the compound is administered every 6 weeks (about 1 and a half months), 7 weeks, 8 weeks (about 2 months), 9 weeks, or 10 weeks (about 2 and a half months).


In another embodiment of the invention, it was surprisingly discovered that the compounds of the invention provide 80% efficacy as early as 3 days after administration and provide long lasting efficacy. For a number of compounds such early onset of activity against ticks was observed even after topical administration.


In yet other embodiments of the invention, the compounds provide an early onset of activity, this means 80% or more efficacy as early as 3 days or, less than 3 days, e.g., 2 days or 1 day after administration.


The fast acting and long-lasting control provided by the compounds of the current invention is unexpected.


In another aspect the present invention thus provides a pharmaceutical composition comprising an effective amount of one or more, preferably one compound according to the invention and one or more pharmaceutically acceptable excipients.


The compounds according to this invention are useful in controlling parasitic infestations of animals. One of ordinary skill in the art typically can determine an “effective” dose by, for example, observing or detecting changes in a clinical condition or behavior of a host animal, as well as by observing or detecting relative changes in parasite numbers after such treatment.


An “effective amount,” is the amount or quantity of a compound that is required to cause a measurable reduction in the ectoparasite population infesting an animal, and/or to inhibit the development of parasite infestations of an animal, in whole or in part. Alternatively, this may refer to an amount, dose, or quantity that can effectively control and/or reduce presence of parasites in an animal's housing or its surroundings, e.g., the house, building, farm, fields, etc.


This amount is readily determined by observation or detection of the pathogen numbers such as parasite numbers both before and after contacting the sample of pathogens such as parasites including their stages with the compound according to this invention, directly and/or indirectly, e.g., by contacting articles, surfaces, foliage, or animals with the compound. When the compound shows an effect via feeding/ingestion by the parasite, an effective amount generally constitutes an amount that results in tissue and/or blood concentrations generally toxic when ingested by the target parasite.


To establish that an effective reduction of infestation of an animal, or an effective control and/or reduction of parasites in the surroundings has occurred, and thus: what constitutes such an effective amount, is readily determined by comparing the parasite numbers either on the animal or in an animal's environment, before and after administering a compound as described herein.


Detection can be e.g., done by counting of the number of parasites visible on an animal, or by counting parasites using a trap or other detection-device in the surroundings.


The difference in numbers from such counts made before and after treatment indicates the efficacy of the dose applied e.g., the parasite count is reduced, after a first administration, by an amount ranging from 5% to about 100%.


So, although reductions at—or close to 100% are aimed for, however a reduction in parasite numbers of about 50% may already constitute a significant reduction. This because even such a modest reduction already alleviates certain symptoms for affected animals, and/or may restore the animals to an improved economic production level.


In one embodiment, an effective amount of the active agent achieves at least about 80%, or at least about 90% efficacy against the target parasites. In a specific preferred embodiment, the efficacy is at least about 95%.


In a preferred embodiment, the reduction of infestation on an animal, or the control and/or reduction achieved, regards a reduction in the number of a particular type of parasite by at least 50, 60, 70, 75, 80, 85, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or even 100%, in that order of preference.


Animals to be Treated

The compounds or composition may be used for controlling parasite infestations in a range of animals, especially domestic animals.


As used herein, the term “domestic animal” includes any animal that is kept by humans as a companion animal, pet, working animal or as livestock for food, fur, leather, wool or other animal product; or an animal that is found in association with humans such that control of ectoparasites on such animal is desirable.


In one embodiment such animals are warm-blooded animals. Such warm-blooded animals include poultry animals such as chickens and turkey and mammals, for example, mammals. Mammals include, for example, farm or livestock mammals (e.g., swine, bovines, sheep, goats, etc.), laboratory mammals (e.g., mice, rats, jirds, etc.), companion mammals (e.g., dogs, cats, equines, etc.), fur-bearing animals (e.g., minks, foxes, chinchillas, rabbits, etc.), and wild and zoo mammals (e.g., buffalo, deer, etc.).


The compounds according to the present invention are particularly useful for livestock animals, kept for meat and milk or wool or alternatively as working animals, especially ruminants such as cattle, sheep, goat, deer, camels, lamas.


In one embodiment the animals are bovine animals such as cattle. In this specification, bovine animals are ruminant mammals of the genus Bos and include, but are not limited to, cattle, such as steers, heifers, cows (lactating and non-lactating), calves, bulls, and also buffalo. Especially preferred are beef cattle, i.e., cattle animals kept for meat or alternatively dairy cows. In another embodiment the animals are sheep. In another embodiment the animals are goats.


In another preferred embodiment, the methods and compositions of the invention are used for the treatment prevention of parasitic infections and infestations in ruminants, especially cattle or sheep. When treating livestock animals such as cattle or sheep, the methods and compositions are particularly effective against one host ticks, especially Rhipicephalus (Boophilus) microplus,


In some embodiments, the compounds are used to treat companion animals, especially canine or feline animals. In one embodiment are used to treat canines (e.g., domestic dogs). In other embodiments, the compounds are used to treat felines (e.g., domestic cats).


In a preferred embodiment, the invention provides methods and compositions for the treatment or prevention of parasitic infections and infestations in companion animals including, but not limited to, cats and dogs. The methods and compositions are particularly effective for preventing or treating parasitic infestations of cats and dogs with fleas and/or ticks.


The compounds also are suitable to treat warm-blooded non-mammals, such as poultry (e.g., turkeys, chickens, geese, ducks, parrots, etc.).


In one embodiment the compounds are used to treat cold-blooded animals, such as fish (e.g., salmon, trout, sea bass, sea bream or ornamental fish such as koi, etc.). Therefore, in one embodiment such animals are fish.


In a preferred embodiment the treated fish is salmon. The term “salmon” within the scope of this invention will be understood as comprising all representatives of the family Salmonidae, especially of the subfamily Salmoninae, and preferably, the Atlantic salmon (Salmo solar), rainbow trout (Oncorhynchus mykiss), brown or sea trout (S. trutta).


The compounds for use in the invention can be made available during a treatment period to a single animal.


Especially for livestock animals more advantageous is the treatment at the same time of a group of animals, or to all animals in a single stable, pen, net, group, house, or farm. For companion animals preferably all animals at risk of a parasite infestation are treated at the same time.


A single administration of a compound according to this invention or a compound corresponding to the use according to the invention is typically sufficient to treat a parasitic infestation. Although such a single dose is typically preferred, it is contemplated that multiple doses can be used.


The frequency of the administration will be dependent upon several factors and can be a single dose administered once a day, once a week, once a month, once every two, three, four, or six months, or one every year. In some embodiments, the frequency of administration may be, for example, weekly, bi-weekly, monthly, bi-monthly, every 3 month, every 4 month, every 5 month, every 6 month or every 12 month or the equivalent administration frequency expressed in days or weeks that approximate such frequency.


The duration of activity or efficacy (i.e., “knockdown,” onset of activity and/or sustained effects) can be the primary concern in antiparasitic product choices. Products are evaluated based on both their immediate and residual speed of kill and duration of efficacy. A rapid residual speed of kill, sometimes called onset of activity/efficacy is critically important when attempting to reduce the chances of a tick parasite transmitting a pathogen. The durations over which the compounds are effective against various ectoparasites is important for the required treatment interval. This is particularly important, especially considering that such long activities are obtained when using low doses that are non-toxic to the target animal.


In one embodiment, the composition exhibits long lasting efficacy and provides protection against parasites in livestock animals for at least one month.


In another embodiment, the compounds of the invention exhibit very long-lasting efficacy of at least 50% against ticks that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months.


In another embodiment, the compounds of the invention exhibit very long-lasting efficacy of at least 70% against ticks that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months.


In another embodiment, the compounds of the invention exhibit very long-lasting efficacy of at least 90% against parasites such as e.g. ticks that for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months.


Therefore, one embodiment of the invention is a method wherein the compound is administered every month.


Therefore, in another embodiment of the invention the compound is administered every 6 weeks.


Therefore, in another embodiment of the invention the compound is administered every 2 months.


Therefore, in another embodiment of the invention the compound is administered every 3 months.


In one embodiment an effective dose of the compound protects animals, especially cattle from infestation or re-infestation by parasites such as e.g., ticks, mites, lice and/or biting flies for at least 48 days.


Therefore, in one embodiment of the invention the compound is administered every 6 weeks (about 1 and a half months), 7 weeks, 8 weeks (about 2 months), 9 weeks, or 10 weeks (about 2 and a half months).


In another embodiment of the invention, it was surprisingly discovered that the compounds of the invention provide 80% efficacy as early as 2 to 6 days after administration and provide long lasting efficacy. For a number of compounds such early onset of activity against ticks was observed even after topical administration.


In yet other embodiments of the invention, the compounds provide an early onset of activity, this means 80% or more efficacy as early as 3 days or 2 days or 1 day after administration.


The fast acting and long-lasting control provided by the compounds of the current invention is unexpected.


The compounds for use in the invention can be made available during a treatment period to a single animal.


Especially for livestock animals more advantageous is the treatment at the same time of a group of animals, or to all animals in a single stable, pen, net, group, house, or farm. For companion animals preferably all animals at risk of a parasite infestation are treated at the same time.


Generally, a dose of from about 0.001 to about 100 mg per kg of body weight given as a single dose will be used but, of course, there can be instances where higher or lower dosage ranges are indicated, and such are within the scope of this invention.


In some embodiments, for example, from about 0.01 to about 100 mg/kg body weight is administered.


In other embodiments, for example, from about 0.01 to about 50 mg/kg body weight is administered.


In some such embodiments, for example, from about 0.1 to about 40 mg/kg body weight is administered.


In other such embodiments, from about 1 to about 30 mg/kg body weight is administered. Greater dosages tend to provide for greater duration of activity/efficacy.


Factors affecting the preferred dosage may include, for example, the parasite species infestation to be treated and the development stages of the parasites, the type (e.g., species and breed), age, size, sex, diet, activity, and condition of the infected animal; the dosage route; pharmacological considerations, such as the activity, efficacy, pharmacokinetic, and toxicology profiles of the particular composition administered; and whether the compound according to this invention being administered as part of a combination of active ingredients. Thus, the preferred amount of the compound according to this invention can vary, and, therefore, can deviate from the typical dosages set forth above.


For many animals, the dose and composition comprising the compounds are chosen to maintain a blood level of at least about 30 ng/ml, more preferably about 40 ng/ml, about 50 ng/ml, or 60 ng/ml.


In some embodiments, the concentration of the compounds in the plasma that is sufficient to obtain at least 80% efficacy against ticks is less than or equal to about 60 ng/ml.


Generally, a dose of from about 0.001 to about 100 mg per kg of body weight given as a single dose or in divided doses for a period of from 1 to 5 days will be satisfactory but, of course, there can be instances where higher or lower dosage ranges are indicated, and such are within the scope of this invention.


When compounds according to this invention is orally administered, the total dose is generally greater than about 0.01 mg/kg (i.e., milligram of compound according to this invention per kilogram body weight of the treated animal). The oral administration of compounds has been surprisingly shown to protect animals from parasite infestation, especially dogs from flea and/or tick infestation for an exceptionally long period.


Therefore, in one embodiment the compound is administered orally to the animal, especially dog to protect the animal from parasite infestation, especially from fleas and or ticks, preferably from fleas and ticks.


In some such embodiments, the total dose is from about 0.01 to about 100 mg/kg, from about 0.01 to about 50 mg/kg, from about 0.1 to about 25 mg/kg, or from about 1 to about 20. For sheep, for example, the dose is generally from about 0.5 to about 15 mg/kg, from about 1 to about 10 mg/kg. The same dose range may be suitable for other dosage routes.


For example, in some embodiments, a higher dose range is used for topical pour on administration.


In one embodiment the compound is administered by topical pour on administration to the animal, especially cattle to protect the animal from parasite infestation, especially from acaride parasites, preferably from ticks.


For example, in some embodiments, the same dose range is used for subcutaneous administration.


In one embodiment the compound is administered by injection, especially subcutaneous administration to the animal, especially cattle to protect the animal from parasite infestation, especially from acaride parasites, preferably from ticks.


If the compound according to this invention is administered parenterally via an injection, especially via subcutaneous administration the concentration of the compound according to this invention in the dosage form preferably is sufficient to provide the desired effective amount of the compound according to this invention in a volume that is acceptable for parenteral administration. Furthermore, no severe injection site reaction should be resulting from such injection.


In some embodiments, one or more, preferably one compound according to this invention is used to control an infestation by a parasite, especially ectoparasite, especially tick that is resistant to one or more commercially available and known existing parasiticide compounds.


Therefore, the compounds of the current invention can be used on animals that are infested or at risk of infestation with parasites, especially ticks, that are resistant to any one of organophosphates, synthetic pyrethroids, or benzoyl phenyl urea compounds and will still provide effective treatment/protection.


Factors affecting the preferred dosage may include, for example, the parasite species infestation to be treated and the development stages of the parasites, the type (e.g., species and breed), age, size, sex, diet, activity, and condition of the infected animal; the dosage route; pharmacological considerations, such as the activity, efficacy, pharmacokinetic, and toxicology profiles of the particular composition administered; and whether the compound according to this invention being administered as part of a combination of active ingredients. Thus, the preferred amount of the compound according to this invention can vary, and, therefore, can deviate from the typical dosages set forth above.


For many animals, the dose and composition comprising the compounds are chosen to maintain a blood level of at least about 30 ng/ml, more preferably about 40 ng/ml, about 50 ng/ml, or 60 ng/ml.


In some embodiments, the concentration of the compounds in the plasma that is sufficient to obtain at least 80% efficacy against ticks is less than or equal to about 60 ng/ml.


Administration Routes

When compounds according to this invention is orally administered, the total dose is generally greater than about 0.01 mg/kg (i.e., milligram of compound according to this invention per kilogram body weight of the treated animal).


In some such embodiments, the total dose is from about 0.01 to about 100 mg/kg, from about 0.01 to about 50 mg/kg, from about 0.1 to about 25 mg/kg, or from about 1 to about 20. For sheep, for example, the dose is generally from about 0.5 to about 15 mg/kg, from about 1 to about 10 mg/kg. The same dose range may be suitable for other dosage routes.


For example, in some embodiments, a higher dose range is used for topical pour on administration.


For example, in some embodiments, the same dose range is used for subcutaneous administration.


If the compound according to this invention is administered parenterally via an injection, especially via subcutaneous administration the concentration of the compound according to this invention in the dosage form preferably is sufficient to provide the desired therapeutically effective amount of the compound according to this invention in a volume that is acceptable for parenteral administration. Furthermore, no severe injection site reaction should be resulting from such injection.


In some embodiments, one or more, preferably one compound according to this invention is used to control an infestation by a parasite, especially ectoparasite, especially tick that is resistant to one or more commercially available and known existing parasiticide compounds.


Therefore, the compounds of the current invention can be used on animals that are infested or at risk of infestation with parasites, especially ticks, that are resistant to any one of organophosphates, synthetic pyrethroids, or benzoyl phenyl urea compounds and will still provide effective treatment/protection.


Dosage Form

The compounds according to this invention may be administered in various dosage forms.


The term “dosage form” means that the compounds according to this invention are formulated into a product suitable for administering to the animal via the envisaged administration route. Such dosage forms are sometimes referred to herein as formulations or pharmaceutical composition.


The formulation type chosen for a dosage form in any instance will depend upon the particular purpose envisaged and the physical, chemical, and biological properties of the compound according to this invention.


The invention is also directed to a veterinary composition comprising an effective amount of a compound of Formula (I) as defined in any embodiment described herein and an inert carrier or formulation adjuvant. The composition is suitable for use in the treatment and control of a parasitic infestation of animals such as described herein.


Suitably the veterinary composition is a topical composition, an oral composition, or an injection composition.


The present invention is also directed to a veterinary composition comprising an effective amount of a compound of Formula (I) as defined in any embodiment described herein and an inert carrier or formulation adjuvant. Suitably the composition is used in the treatment and control of a parasitic infestation of animals as described herein.


In an embodiment of the invention and/or embodiments thereof, the veterinary composition is a topical composition.


In an embodiment of the invention and/or embodiments thereof, the veterinary composition is an oral composition.


In an embodiment of the invention and/or embodiments thereof, the veterinary composition is an injection composition.


In another aspect the present invention thus provides a pharmaceutical composition comprising an effective amount of one or more, preferably one compound according to the invention and one or more pharmaceutically acceptable excipients.


The term “excipient,” “diluent” or “carrier” is used herein to describe any ingredient other than the Formula (I) compounds or any additional antiparasitic agent in a dosage form. The choice of excipient, diluent, or carrier will to a considerable extent depend on factors such as the particular route and mode of administration, the effect of the excipient, carrier, or diluent on solubility and stability, and the nature of the dosage form.


Pharmaceutically acceptable as used in this application, for example with reference to salts and composition components such as carriers, includes “dermatologically acceptable” for topical dosage forms, and “veterinary acceptable,” and thus includes both human and animal applications independently.


Dosage forms useful in the current invention can be liquid, semi-solid or solid dosage forms.


Liquid dosage forms of the compounds are generally solutions, suspensions, or emulsions. A solution is a mixture of two or more components that form a single phase that is homogeneous down to the molecular level. A suspension consists of insoluble solid particles dispersed in a liquid medium, with the solid particles accounting for about 0.5% to about 30% of the suspension. The liquid may be aqueous, oily, or both. An emulsion is a heterogeneous dispersion of one immiscible liquid in another; it relies on an emulsifying agent for stability.


A dry powder (or granule) for reconstitution is reconstituted as a solution or as a suspension immediately prior to injection. The principal advantage of this dosage form is that it overcomes the problem of instability in solution or suspension.


One possible administration route is the oral route, wherein the compound according to this invention is administered via the mouth. Oral dosage forms suitable for oral administration comprise liquids (e.g., drench or drinking water formulations), semi-solids (e.g., pastes, gels), and solids (e.g., tablets, capsules, powders, granules, chewable treats, premixes, and medicated blocks).


A number of veterinary compositions are known to be suitable for oral administration to animals, but they vary for the different animal species. For sheep conventionally pharmaceutically active ingredients are administered orally as solids (e.g., tablets or boluses) or liquids, and via their feed or drinking water. In large sheep and cattle flocks the use of oral drenches is the most common oral dosage form, especially when administering anthelmintic compounds.


Drenching means that a liquid, potentially slightly viscous composition comprising the compound and excipients is applied via the mouth with a specific drenching gun that dispenses a compound into the sheep's throat.


A drench is a liquid oral formulation that is administered directly into the mouth/throat of an animal, especially a livestock animal, by means of a “drench gun” or syringe or another suitable device. When the composition is administered in the animal recipient's drinking water or as a drench, it may be convenient to use a solution or suspension formulation. This formulation can be, for example, a concentrated suspension that is mixed with water or a dry preparation that is mixed and suspended in the water.


Semi-solid oral formulations (pastes or gels) are generally administered via an applicator directly into the mouth of an animal or mixed with the feed.


Solid oral formulations are either administered directly to an animal (tablet, capsule, bolus) or mixed with the feed or via medicated feed blocks.


When the oral formulation is administered via a non-human animal's feed, it may, for example, be fed as a discrete feed or as a chewable treat. Alternatively (or additionally), it may, for example, be intimately dispersed in the animal recipient's regular feed, used as a top dressing, or in the form of solid pellets, paste or liquid that is added to the finished feed. When the oral formulation is administered as a feed additive, it may be convenient to prepare a “premix” in which the oral formulation is dispersed in a liquid or solid carrier. This “premix” is, in turn, dispersed in the animal's feed using, for example, a conventional mixer in order to ensure a more homogeneous distribution of the compound in the feed.


Several modified-release delivery systems have been developed, that take advantage of the unique anatomy of the ruminant forestomach, i.e., for intra-ruminal administration. An intraruminal bolus is a specific formulation for ruminants (cattle, sheep, goats, buffalos, camelids, deer etc.). It is a veterinary delayed release delivery system which remains in the rumeno-reticular sac of a ruminant animal over an extended period of time and in which the therapeutically active substance has a predictable and delayed release pattern. Such intraruminal boluses are usually administered using a balling gun or another suitable device.


Compounds according to this invention may alternatively be administered via non-oral dosage routes, such as topically (e.g., via a spot-on, pour-on, spray), or parenterally (e.g., subcutaneous injection, intravenous injection, intramuscular injection, etc.).


For instance, the compounds according to this invention may be administered topically using a transdermal formulation (i.e., a formulation that passes through the skin).


Topical dosage forms suitable for topical administration comprise liquids (e.g., bath, spray, spot-on), semi-solids (e.g., creams, gels), and solids (e.g., patches, powders, collars). Typical topical formulations for animals are liquid or semi-liquid dosage forms.


Typical formulations for topical and transdermal administration include, for example, pour-ons, spot-ons, dips, sprays, mousses, shampoos, powders, gels, hydrogels, lotions, solutions, creams, ointments, dusting powders, dressings, foams, films, skin patches, limb bands, collars, ear tags, wafers, sponges, fibers, bandages, and microemulsions. When a liquid formulation is used topically on skin, it can be administered by, for example, pouring on (pour-on or spot-on), spreading, rubbing, atomizing, spraying, dipping, bathing, or washing.


The pour-on or spot-on methods, for example, comprise applying the formulation to a specific location of the skin or coat, such as on the neck or backbone of the animal. This may be achieved by, for example, applying a swab or drop of the pour-on or spot-on formulation to a relatively small area of the recipient animal's skin or coat (i.e., generally no greater than about 10% of the animal recipient's skin or coat). In some embodiments, the compound according to this invention is dispersed from the application site to wide areas of the fur due to the spreading nature of the components in the formulation and the animal's movements while, in parallel, being absorbed through the skin and distributed via the animal recipient's fluids and/or tissues.


Parenteral formulations and delivery systems for non-oral routes comprise liquids (e.g., solutions, suspensions, emulsions, and dry powders for reconstitution), semi-solids and solids (e.g., implants). The majority of implants that are used in veterinary medicine are compressed tablets or dispersed matrix systems in which the drug is uniformly dispersed within a biodegradable or nondegradable polymer or are extrusion products.


PHARMACEUTICAL COMPOSITIONS

This invention also is directed to pharmaceutical compositions (or medicaments) comprising one or more, preferably one compound according to this invention. The compositions also may (and preferably will) comprise one or more pharmaceutically acceptable excipients. The following subject matter about pharmaceutical compositions is also applicable to pharmaceutical compositions comprising compounds corresponding to the use according to this invention.


Pharmaceutical compositions of the present invention may be manufactured by, for example, processes known in the art. These processes include, for example, a variety of known mixing, dissolving, granulating, emulsifying, encapsulating, entrapping, and lyophilizing processes. Optimal formulation depends on, for example, the dosage route (e.g., oral, parenteral by injection, topical).


Solid dosage forms, for example, may be prepared by, for example, intimately and uniformly mixing the compounds with fillers, binders, lubricants, glidants, disintegrants, flavoring agents (e.g., sweeteners), buffers, preservatives, pharmaceutical-grade dyes or pigments, and controlled release agents.


Oral dosage forms other than solids may be prepared by mixing the compounds with, for example, one or more solvents, viscosity-enhancing agents, surfactants, preservatives, stabilizers, resins, fillers, binders, lubricants, glidants, disintegrants, co-solvents, sweeteners, flavorings, buffers, suspending agents, and pharmaceutical-grade dyes or pigments.


Contemplated binders include, for example, starch, gelatin, acacia, and carboxymethyl cellulose.


Contemplated lubricants include, for example, magnesium stearate, stearic acid, and talc.


Contemplated disintegrants include, for example, corn starch, alginic acid, sodium carboxymethylcellulose, and sodium croscarmellose.


Contemplated buffers include, for example, sodium citrate, and magnesium and calcium carbonate and bicarbonate.


Contemplated solvents include, for example, water, pyrrolidone solvents, vegetable oils, mineral oil, and synthetic oil such as medium chain triglycerides e.g., Miglyol 812 or 840. Physiological saline solution or glycols (e.g., propylene glycol, or polyethylene glycol) also may be included. The solvent preferably has sufficient chemical properties and quantity to keep the compounds solubilized at temperatures in which the composition is stored and used.


Contemplated viscosity-enhancing agents include, for example, polyethylene, methylcellulose, sodium carboxymethylcellulose, hydroxypropyl-methylcellulose, hydroxypropylcellulose, sodium alginate, carbomer, povidone, acacia, guar gum, xanthan gum, tragacanth, methylcellulose, carbomer, xanthan gum, guar gum, povidone, sodium carboxymethylcellulose, magnesium aluminum silicate, carboxyvinyl polymers, carrageenan, hydroxyethyl cellulose, laponite, water-soluble salts of cellulose ethers, natural gums, colloidal magnesium aluminum silicate or finely divided silica, homopolymers of acrylic acid crosslinked with an alkyl ether of pentaerythritol or an alkyl ether of sucrose, and carbomers.


Contemplated surfactants include, for example, sodium lauryl sulfate, polyoxyethylene sorbitan fatty acid esters; polyoxyethylene monoalkyl ethers; sucrose monoesters; lanolin esters and ethers; alkyl sulfate salts; and sodium, potassium, and ammonium salts of fatty acids.


Contemplated preservatives include, for example, phenol, alkyl esters of parahydroxybenzoic acid (e.g., methyl p-hydroxybenzoate (or “methylparaben”) and propyl p-hydroxybenzoate (or “propylparaben”)), sorbic acid, o-phenylphenol benzoic acid and the salts thereof, chlorobutanol, benzyl alcohol, thimerosal, phenylmercuric acetate and nitrate, nitromersol, benzalkonium chloride, and cetylpyridinium chloride.


Contemplated stabilizers include, for example, chelating agents and antioxidants.


Solid dosage forms also may comprise, for example, one or more excipients to control the release of the compounds. For example, it is contemplated that the compounds may be dispersed in, for example, hydroxypropylmethyl cellulose. Some oral dosage forms (e.g., tablets and pills) also may be prepared with enteric coatings.


Topical dosage route uses, for example, a concentrated liquid or semi-liquid solution, suspension (aqueous or non-aqueous), emulsion (water-in-oil or oil-in-water), or microemulsion comprising a compound dissolved, suspended, or emulgated in a pharmaceutically acceptable liquid vehicle. In such embodiments, a crystallization inhibitor optionally may generally be present.


Such a pour-on or spot-on formulation can be prepared by dissolving, suspending, or emulsifying the compounds in a suitable skin-fitted solvent or solvent mixture. Other excipients may be included as well, such as, for example, a surfactant, colorant, antioxidant, stabilizer, adhesive, etc. Contemplated solvents include, for example, water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oil, DMF, liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone, or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.


In some embodiments, a topical formulation (particularly a pour-on or spot-on formulation) comprises a carrier that promotes the absorption or penetration of the compounds through the skin into the blood stream, other bodily fluids (lymph), and/or body tissue (fat tissue). Contemplated examples of dermal penetration enhancers include, for example, dimethylsulfoxide, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides, and fatty alcohols.


Topical formulations also (or alternatively) may comprise, for example, one or more spreading agents. These substances act as carriers that assist in distributing an active ingredient over the animal recipient's coat or skin. They may include, for example, isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, and/or fatty alcohols. Various spreading oil/solvent combinations also may be suitable, such as, for example, oily solutions, alcoholic and isopropanolic solutions (e.g., solutions of 2-octyl dodecanol or oleyl alcohol), solutions of esters of monocarboxylic acids (e.g., isopropyl myristate, isopropyl palmitate, lauric acid oxalic ester, oleic acid oleyl ester, oleic acid decyl ester, hexyl laurate, oleyl oleate, decyl oleate, and caproic acid esters of saturated fatty alcohols having a carbon chain of 12 to 18 carbons), solutions of esters of dicarboxylic acids (e.g., dibutyl phthalate, diisopropyl isophthalate, adipic acid diisopropyl ester, and di-n-butyl adipate), or solutions of esters of aliphatic acids (e.g., glycols). When the formulation comprises a spreading agent, it also may be advantageous to include a dispersant, such as, for example, pyrrolidin-2-one, N-alkylpyrrolidin-2-one, acetone, polyethylene glycol or ether or ester thereof, propylene glycol, or synthetic triglycerides.


Injectable formulations may be prepared according to, for example, the known art using suitable solvents, solubilizing agents, protecting agents, dispersing agents, wetting agents, and/or suspending agents. Contemplated carrier materials include, for example, water, ethanol, butanol, benzyl alcohol, glycerin, 1,3-butanediol, Ringer's solution, isotonic sodium chloride solution, bland fixed oils (e.g., synthetic mono- or diglycerides), vegetable oil (e.g., corn oil), fatty acids (e.g., oleic acid), dimethyl acetamide, surfactants (e.g., ionic, and non-ionic detergents), N-methylpyrrolidone, propylene glycol, and/or polyethylene glycols (e.g., PEG 400). Contemplated solubilizing agents include, for example, polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester, and the like. Contemplated protecting agents include, for example, benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol, and the like.


In some embodiments, a parenteral formulation is, for example, prepared from sterile powders or granules having one or more of the carrier materials discussed above for other formulations. The compound is, for example, dissolved or suspended in a liquid comprising water, polyethylene glycol, propylene glycol, ethanol, corn oil, cottonseed oil, peanut oil, sesame oil, benzyl alcohol, sodium chloride, and/or various buffers. The pH generally may be adjusted, if necessary, with a suitable acid, base, or buffer.


Further aspects regarding formulation of drugs and various excipients are found in, for example, Gennaro, A. R., et al., eds., Remington: The Science and Practice of Pharmacy (Lippincott Williams & Wilkins, 20th Ed., 2000).


The concentration of the compounds according to this invention in the applied dosage form may vary widely depending on, for example, the dosage route. In general, the concentration in the dosage form is from about 1 to about 70% (by weight). In some such embodiments, for example, the concentration is from about 1 to about 50% (by weight), or from about 10 to about 50% (by weight). In other embodiments, the concentration is from about 35 to about 65% (by weight), from about 40 to about 60% (by weight), from about 45 to about 55% (by weight), or about 50% (by weight).


In another aspect the present invention thus provides a pharmaceutical composition comprising an effective amount of one or more, preferably one compound according to this invention and one or more pharmaceutically acceptable excipients.


The formulation type chosen for a dosage form in any instance will depend upon the particular purpose envisaged and the physical, chemical, and biological properties of the compound according to this invention.


TOPICAL PHARMACEUTICAL COMPOSITIONS

In one embodiment the compound of Formula (I)-(XCII) according to the invention and/or embodiments thereof is administered topically to an animal, preferably by pour-on or spot-on administration.


In another aspect of the invention and/or embodiments thereof, a use or method for protecting an animal from or treating a parasite infestation/infection in an animal is provided, comprising administering to the animal a topical composition comprising an effective amount of at least one compound of the invention together with a pharmaceutically acceptable carrier that is suitable for application to the skin of the animal.


In some embodiments of the invention, the topical compositions are formulated to control the rate of permeation of the compound in order to maintain efficacious levels of the active in the plasma for a prolonged period of time and significantly extend the duration of efficacy.


In a specific embodiment the current invention is directed to a veterinary pharmaceutical composition comprising a compound of Formula (I) according to the invention and/or embodiments thereof and a pharmaceutically acceptable oily carrier.


The topical composition is administered to the animal in an amount of about 0.5 mg to about 10 mg, even more typically about 1 mg to about 2.5 mg, of the compound of Formula (I)-(XCII) according to the invention and/or any embodiment thereof, especially of compound according to formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa) per kg bodyweight of the treated animal.




embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.







embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.







embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.







embedded image




    • and N-oxides, veterinary acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers, and tautomers thereof.





However, as will be apparent to a person skilled in the art, the effective amount to control particular parasites of an animal will vary depending on a number of factors including, for example, the particular compound of Formula (I) in the composition, the species of animal, the age, sex and health of the animal, the particular parasites infesting the animal and the severity of parasitic infestation. For any given case, a person skilled in the art could readily determine an effective amount using standard techniques and routine experimentation.


The composition of the present invention includes as a pharmaceutically effective oily carrier.


“Pharmaceutically or veterinarily acceptable carrier” means a carrier that is useful in preparing a pharmaceutical composition that is generally safe, non-toxic, and neither biologically nor otherwise undesirable, and includes a carrier that is acceptable for veterinary use or pharmaceutical use.


As used herein, by an “oily carrier” means a carrier that used an oil as a solvent for dissolving the compound or, otherwise, adopts oil as a medium for dispersing or suspending the compound in a powder form, which is insoluble in the oil. It is meant that an oil constitutes at least 50% by weight of the total amount of the carrier and may include additional nonvolatile co-solvent or co-solvents.


In a preferred embodiment an oil constitutes at least 99% to 99.5% by weight of the total amount of the carrier.


According to the present invention, the oil may be a solvent in which the compound of Formula (I)-(XCII) and/or embodiments thereof, is dissolved, dispersed and/or suspended and may include, for example; monoglyceride, diglyceride, triglyceride, medium chain triglyceride (M CT), sesame oil, arachis oil (peanut oil), castor oil, olive oil, corn oil, cotton seed oil, soybean oil, peppermint oil, coconut oil, palm seed oil, safflower oil, etc., without being particularly limited thereto. These substances may be used alone or as a mixture of two or more thereof.


In a preferred embodiment the carrier consists of a fatty acid ester. Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides.


In an alternative embodiment the oily carrier comprises a fatty acid ester.


Preferably the fatty acid ester is a medium chain triglyceride. Medium chain triglycerides (MCT) have fatty acid chains of 6-12 carbon atoms and for the medically refined grades of MCT oil each chain has 8-10 carbon atoms.


The MCT oil may comprise either triglycerides of the C8-C10 fatty acids, or propylene glycoldiesters of these fatty acids or a mixture of both triglycerides and propylene glycol diesters. Preferably these C8-C10 fatty acids are fully saturated, such as n-caprylic and n-capric acids. These are conveniently prepared by the commercial fractionating of naturally occurring vegetable (e.g. coconut) oil to give mainly C8-10 fatty acids followed by esterification of these acids with a chosen alcohol.


Fractionated vegetable oil having the desired composition is commercially available. Proprietary examples of such MCT oils are Miglyol® 812 as capric/caprylic triglycerides and Miglyol® 840 as propylene glycol dicaprylate/caprate. Most preferred is propylene glycol dicaprylate/caprate such as e.g., Miglyol 840.


A preferred additional component is Glycerol Monocaprylate, e.g. commercially available as Imwitor®988.


It has been found that a particular group of MCT oils has the combined properties of low irritancy and appropriate solvency and is particularly suitable for use in compositions for localised topical application of the compound.


These medium chain fatty acid ester have the additional advantages of having low melting points and it has been surprisingly found that Miglyol 840 results in a very high level of transdermal penetration of the compound of Formula (I) according to the invention and/or any embodiment thereof.


Specifically, the invention relates to a composition according to the invention comprising of compound according to formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa) as described above dissolved in a mixture of glycerol and propylene glycol esters of fatty acids.


One example of a composition according to the invention consists of 1% w/v of compound according to formula (I) of the invention and/or embodiments therof and 99% w/v propylene glycol dicaprylocaprate.


Another example of a composition according to the invention consists of 1% w/v of compound according to formula (I) according to the invention and/or embodiments thereof, 20% w/v glycerol monocaprylate, and 79% w/v propylene glycol dicaprylocaprate.


One example of a composition according to the invention consists of 1% w/v of compound according to formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa), preferably compound of formula (LXI) or formula (LXIa), and 99% w/v propylene glycol dicaprylocaprate.


Another example of a composition according to the invention consists of 1% w/v of compound according to formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa), preferably compound of formula (LXI) or formula (LXIa), 20% w/v glycerol monocaprylate, and 79% w/v propylene glycol dicaprylocaprate.


The examples show how, contrary to many topical solutions (such as e.g., the commercial pour-on product Dectomax from Zoetis) the composition of the invention does not require rapid solvent evaporation on application to have good maximum absorbance (Cmax) and total absorbance (AUC).


In particular compositions of the invention, the glycol or glycerol ester of a C8-10 fatty acid in the carrier is present in an amount from about 50 to about 99.9% by weight of the composition, particularly, from about 79 to about 99.5%, from about 85 to about 99%.


Typically, the composition comprises from about 0.5% to about 10% w/v, preferably 1% of the compound of Formula (I), b) from about 10% to about 40% w/v, preferably 20% of glycerol monocaprylate; and c) optionally from about 2% to about 50% w/v, preferably 79% of propylene glycol dicaprylocaprate.


In accordance with this invention, it has been discovered that the compositions according to the invention generally show one or more beneficial technical features including desirable transdermal bioavailability.


It has been discovered that a single administration of such compositions generally provides potent activity against one or more ectoparasites, while also tending to provide fast onset of activity, long duration of activity, and/or desirable safety profiles toward the host animals and animal caretaker. Furthermore, the compositions are easy to administer to the animals and have s desirable transdermal bioavailability and spectrum of coverage. Preferably effective blood levels are obtained by the administration of the composition according to the invention.


An example of a species where this invention would be useful in the prevention of parasites is on cattle. Cattle skin is known to be especially difficult for transdermal administration and surprisingly this oily carrier of a compound of Formula (I) is highly effective.


The transdermal liquid preparation according to the invention has a desirable absolute systemic bioavailability to facilitate this excellent and long duration efficacy against ectoparasites.


It was surprisingly found that the topical compositions of the invention comprising a compound provide excellent efficacy against ticks. In some embodiments, the topical compositions of the invention comprising selected solvents and excipients result in effective levels of the active compound over a prolonged period of time.


Conventionally pour-on compositions that show systemic bioavailability require the presence of penetration enhancersin the composition (also called permeation enhancer, sorption promoters or accelerants) which penetrate into skin to reversibly decrease the barrier resistance. Numerous compounds have been evaluated for penetration enhancing activity, including sulphoxides (such as dimethylsulphoxide, DMSO), azones (e.g., laurocapram), pyrrolidones (for example 2-pyrrolidone), alcohols and alkanols (ethanol, or decanol), glycols (for example propylene glycol, PG, a common excipient in topically applied dosage forms), surfactants and terpene or fatty acids.


Therefore, it was unexpected to obtain effective blood levels after pour-on administration of the composition of the invention without the need to include any such permeation or penetration enhancer.


It has been observed that the addition of a permeation/penetration enhancer does not provide any significant advantage as to the effectiveness of the composition according to the invention.


Unexpectedly, the pharmaceutical composition resulted in both bioavailability after transdermal administration and therapeutic and prophylactic efficacy against an infestation of against artificially acquired burdens of cattle tick Rhipicephalus microplus ticks.


Such effective blood concentrations are already reached 2 days after administration and were further maintained for a prolonged period of time, especially more than 70 days, at least 11 weeks, or more than 2.5 months.


In another embodiment the composition exhibits long lasting efficacy of at least 90% against ticks, mites or lice for a period of at least 6 weeks.


One embodiment of the invention is a method wherein the composition is administered every month. In another embodiment of the invention the composition is administered every six weeks. In another embodiment of the invention the composition is administered every 2 months. In another embodiment of the invention the composition is administered every 3 months.


The compositions according to the invention are outstandingly suitable for use in parasite control or parasite prophylaxis. Thus, the pharmaceutical compositions described here serve for use in the treatment of or prophylaxis of parasite infestation, especially in the treatment of or prophylaxis of ectoparasites.


The compositions according to the invention are particularly suitable in the control of or prophylaxis of ectoparasites, preferably of ticks and/or mites, and/or flies or fly larvae, and/or lice, on non-human animals, particularly warm-blooded animals, preferably mammals. In one preferred embodiment the non-human animal is a ruminant e.g., animals such as cattle sheep and goats, especially cattle animal, such as a dairy cow, beef cattle or breeding stock.


According to a particularly preferred embodiment the present compositions are used in the control of and/or prophylaxis of ectoparasites of cattle such as infestation or re-infestation by ticks, mites, lice and/or biting flies. In a preferred embodiment the composition of the invention comprising compounds of Formula (I) is administered by pour-on administration to cattle animal to control ticks, especially R. microplus.


The pour-on composition according to the invention is a liquid and has a sufficient viscosity that prevents run-off from the animals' fur or skin by sufficient adherence to the fur/skin of the animal after administration, but can be easy administered, e.g., expelled the correct amount from the container at various temperatures.


The pour on composition dry within a reasonable period of time without impairment of the animal's appearance, is gentle on the animal's coat, has acceptable irritancy to the animal's skin and maintain its effectiveness on the animal through normal activities of the animal, such as exposure to sun and water.


The inventors have also found that compositions according to the current invention are also advantageously “rainfast”, that is, the composition is effective in controlling parasites of an animal even when applied to a wet animal and is effective in controlling parasites even when the animal is exposed to rain shortly after topical application of the composition of the invention.


This means that the therapeutic efficacy for parasites is not affected by heavy rainfall (such as e.g., 25 mm) either before (20 minutes) or after (20 and 40 minutes) administration to the animal.


Consequently, in one aspect the current invention is directed to the veterinary pharmaceutical composition according to the current invention wherein the composition is rainfast by showing therapeutic efficacy for parasites is not affected by heavy rainfall either before or after treatment.


The volume of the topical composition as a spot-on or pour-on applied should be practical and shown to be safe and effective. Typically, the volume applied depends on the size and weight of the animal as well as the concentration of active. It is preferred to apply a volume that allows accurate dosing but does not result in run-off of the composition, especially if the animal moves.


For the pour-on form of the composition, the volume applied can be of the order of about 0.3 to about 100 ml. In other embodiments, volume applied of the pour-on compositions may be about 1 ml to about 100 ml or about 1 ml to about 50 ml. In still other embodiments, the volume may be about 5 ml to about 50 ml or about 10 ml to about 100 ml.


Preferably for cattle and sheep animals a volume of 10 ml or less per animal of the pour-on-on composition is administered. Generally, pour-on on compositions have a higher viscosity than compositions for spot-on applications and in one embodiment comprise a viscosity increasing component.


In one embodiment the application volume is 1 ml of the composition per 10 kg of the animal bodyweight. In another embodiment the application volume is 1 ml of the composition per 20 kg of the animal bodyweight.


The topical localized spot-on composition is applied as a low volume of about 0.01 to 1 ml per kg, preferably about 0.05 to 0.1 ml per kg, with a total volume from 0.3 to 100 ml per animal depending on the target species.


The pour-on or spot-on compositions according to the invention may be applied using any means known per se, e.g., using an applicator gun or a metering flask, pipette, syringes, roll on, droppers, capsules, foil packages, vials, twist tip containers, metered-dose aerosols or sprays and other single dose and multi-dose containers.


The compositions according to the invention can be prepared by customary methods.


EXAMPLES OF CONTEMPLATED COMBINATION THERAPIES

The methods and pharmaceutical compositions of this invention encompass methods wherein a compound according to this invention is the sole active ingredient administered to the recipient animal. It is contemplated, however, that the methods and pharmaceutical compositions also encompass combination therapies wherein a compound is administered in combination with one or more other pharmaceutically acceptable active ingredients. The other active ingredient(s) may be, for example, one or more other compounds according to this invention or one or more other compounds corresponding to the use according to the invention. Alternatively (or additionally), the other active ingredient(s) may be one or more pharmaceutically acceptable compounds that are not compounds according to this invention or compounds corresponding to the use according to the invention. The other active ingredient(s) may target the same and/or different parasites and conditions.


Contemplated active ingredient(s) that may be administered in combination with the compounds include, for example, pharmaceutically acceptable anthelmintics, insecticides and acaricides, insect growth regulators, anti-inflammatories, anti-infectives, anti-protozoals, hormones, dermatological preparations (e.g., antiseptics and disinfectants), and immunobiologicals (e.g., vaccines and antisera) for disease prevention.


In one embodiment of the description, arylpyrazole compounds such as phenylpyrazoles may be included in the veterinary compositions of the description. Arylpyrazoles are known in the art and may be suitable for combination with the compound of Formula (I) in the compositions of the description. Examples of such arylpyrazole compounds include but are not limited to those described in U.S. Pat. Nos. 6,001,384; 6,010,710; 6,083,519; 6,096,329; 6,174,540; 6,685,954, 6,998,131 and 7,759,381 (all of which are incorporated herein by reference). A particularly preferred arylpyrazole active agent is fipronil.


In another embodiment, the compositions of the description may advantageously include one or more isoxazoline compounds known in the art. Isoxazoline active agents are highly effective against a variety of ectoparasites and combination with the compound of Formula (I) would expand the scope of efficacy against these parasites.


Particularly useful isoxazoline active agents that can be combined with the compound include afoxolaner (including substantially pure active enantiomer), sarolaner, fluralaner (including substantially pure active enantiomer) and lotilaner.


These active agents are described in U.S. Pat. No. 7,964,204, US 2010/0254960 A1, US2011/0159107, US2012/0309620, US2012/0030841, US2010/0069247, WO 2007/125984, WO 2012/086462, U.S. Pat. Nos. 8,318,757, 8,466,115, 8,618,126, 8,822,466, 8,383,659, 8,853,186, 9,221,835, US 2011/0144349, U.S. Pat. No. 8,053,452; US 2010/0137612, U.S. Pat. No. 8,410,153, US 2011/152081, WO 2012/089623, WO 2012/089622, U.S. Pat. Nos. 8,119,671; 7,947,715; WO 2102/120135, WO 2012/107533, WO 2011/157748, US 2011/0245274, US 2011/0245239, US 2012/0232026, US 2012/0077765, US 2012/0035122, US 2011/0251247, WO 2011/154433, WO 2011/154434, US 2012/0238517, US 2011/0166193, WO 2011/104088, WO 2011/104087, WO 2011/104089, US 2012/015946, US 2009/0143410, WO 2007/123855 A2, US 2011/0118212, U.S. Pat. No. 7,951,828 & U.S. Pat. No. 7,662,972, US 2010/0137372 A1, US 2010/0179194 A2, US 2011/0086886 A2, US 2011/0059988 A1, US 2010/0179195 A1, US 2015/0126523, WO 2010/003923, WO 2010/003877, WO 2010/072602, WO 2014/134236, WO 2017/147352, U.S. Pat. Nos. 7,897,630, and 7,951,828, all of which are incorporated herein by reference in their entirety.


Another combination partner is 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide (CAS RN 1621436). This compound is known as tigolaner.


In another embodiment, the compositions of the description may advantageously include one or more SLO-1 modulator compounds known in the art. SLO-1 modulator active agents are highly effective against a variety of parasites and combination with the compound of Formula (I) would expand the scope of efficacy against these parasites. Particularly useful SLO-1 modulator active agents that can be combined with the compound include compounds disclosed in WO2017/178416, WO2018/087036, WO2018/197401, WO2019/002132, WO2019/025341, WO2019115768, WO2019/215182, WO2020/14068, WO2020/131629, WO2020/131631, and WO2020/083971 all of which are incorporated herein by reference in their entirety.


In another embodiment, the compositions of the description may advantageously include one or more SLO-1 depsipeptide compounds known in the art. SLO-1 depsipeptide active agents are highly effective against a variety of parasites and combination with the compound of Formula (I) would expand the scope of efficacy against these parasites. Particularly useful SLO-1 depsipeptide active agents that can be combined with the compound include compounds disclosed in WO2019/108591, WO2019/217449, WO2016/187534, WO2017/116702, WO2018/093920, WO1996/011945, WO1995/007272, WO1994/019334, WO1993/019053, WO2014/089053, WO2018/187173, WO2013/187480, WO2015/093558, WO2012/077783, WO1997/002256, WO1997/011064, U.S. Pat. No. 5,624,897, WO1997/020547, AU2002/226415, JP03207870, DE594082812 all of which are incorporated herein by reference in their entirety.


Therefore, this invention is also directed to the use as a medicament of combinations comprising a) one or more compounds of Formula (I) according to this invention or one with b) one or more pharmaceutically acceptable active compounds which differ in structure from component a).


The active compounds b) are preferably anthelmintic compounds, more preferably selected from the group consisting of SLO-1 depsipeptide compounds and SLO-1 modulators as described above, avermectins (e.g., ivermectin, selamectin, doramectin, abamectin, and eprinomectin); milbemycins (moxidectin and milbemycin oxime); pro-benzimidazoles (e.g., febantel, netobimin, and thiophanate); benzimidazole derivatives, such as triclabendazole or a thiazole benzimidazole derivative (e.g., thiabendazole and cambendazole) or a carbamate benzimidazole derivatives (e.g., fenbendazole, albendazole (oxide), mebendazole, oxfendazole, parbendazole, oxibendazole, flubendazole); an imidazothiazoles (e.g., levamisole and tetramisole); a tetrahydropyrimidine (morantel and pyrantel), organophosphates (e.g., trichlorphon, haloxon, dichlorvos, and naphthalophos); salicylanilides (e.g., closantel, oxyclozanide, rafoxanide, and niclosamide); nitrophenolic compounds (e.g., nitroxynil and nitroscanate); benzenedisulphonamides (e.g., clorsulon); pyrazineisoquinolines (e.g., praziquantel and epsiprantel); heterocyclic compounds (e.g., piperazine, diethylcarbamazine, dichlorophen, and phenothiazine); arsenicals (e.g., thiacetarsamide, melorsamine, and arsenamide); cyclooctadepsipeptides (e.g., emodepside); paraherquamides (e.g. derquantel); and amino-acetonitrile compounds (e.g. monepantel, AAD 1566); tribendimidine (amidine compound); amidine compounds (e.g., amidantel and tribendimidin), including all pharmaceutically acceptable forms, such as salts, solvates or N-oxides.


Preferred combinations are comprising a) one compound selected from the group of compounds according to formula (I) as defined elsewhere in the description, suitably compound 1 to 480 of the table (or enantiomers, salts, solvates, N-oxides or prodrugs thereof) and b) one compound selected from the group consisting of anthelmintic avermectins (e.g., ivermectin, selamectin, doramectin, abamectin, emamectin and eprinomectin); milbemycins (moxidectin and milbemycin oxime); pro-benzimidazoles (e.g., febantel, netobimin, and thiophanate); benzimidazole derivatives, such as thiazole benzimidazole derivatives (e.g., thiabendazole and cambendazole), carbamate benzimidazole derivatives (e.g., fenbendazole, albendazole (oxide), mebendazole, oxfendazole, parbendazole, oxibendazole, flubendazole, and triclabendazole); imidazothiazoles (e.g., levamisole and tetramisole); tetrahydropyrimidines (morantel and pyrantel), organophosphates (e.g., trichlorphon, haloxon, dichlorvos, and naphthalophos); salicylanilides (e.g., closantel, oxyclozanide, rafoxanide, and niclosamide); nitrophenolic compounds (e.g., nitroxynil and nitroscanate); benzenedisulphonamides (e.g., clorsulon); pyrazineisoquinolines (e.g., praziquantel and epsiprantel); heterocyclic compounds (e.g., piperazine, diethylcarbamazine, dichlorophen, and phenothiazine); arsenicals (e.g., thiacetarsamide, melorsamine, and arsenamide); cyclooctadepsipeptides (e.g., emodepside); paraherquamides (e.g. derquantel); amino-acetonitrile compounds (e.g. monepantel, AAD 1566); tribendimidine (amidine compound); and amidantel (amidine compound); including all pharmaceutically acceptable forms, such as salts.


Preferred combinations comprise at least one compound selected from the group of compounds according to formula (I) as defined elsewhere in the description, suitably compound 1 to 480 of the table and

    • abamectin, ivermectin, emamectin, eprinomectin, doramectin, moxidectin, milbemycin oxime; or
    • closantel, oxyclozanide, rafoxanide, niclosamide; or
    • nitroxynil, nitroscanate, clorsulon; or
    • praziquantel, epsiprantel; or
    • emodepside, derquantel, monepantel.


The compounds as described herein can be combined with pharmaceutically acceptable insecticides or acaricides. Such pharmaceutically acceptable insecticides and acaricides include, for example, acetamiprid, acetoprole, amitraz, amidoflumet, avermectin, azadirachtin, bifenthrin, bifenazate, buprofezin, bistrifluron, chlorfenapyr, chlorfluazuron, chlorantraniliprole, chlorpyrifos, chromafenozide, clothianidin, cyantraniliprole, cyflumetofen, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, cymiazole cypermethrin, cyromazine, deltamethrin, demiditraz, diafenthiuron, diazinon, diflubenzuron, dimefluthrin, dinotefuran, emamectin, esfenvalerate, ethiprole, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenoxuron, halofenozide, hexaflumuron, imidacloprid, indoxacarb, lufenuron, metaflumizone, methoprene, metofluthrin, methoxyfenozide, nitenpyram, novaluron, noviflumuron, permethrin, phosmet, profluthrin, protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, tetrachlorvinphos, tetramethylfluthrin, thiacloprid, thiamethoxam, tolfenpyrad, tralomethrin, isoxazolines as described above and triflumuron. General references discussing antiparasitic agents, such as insecticides and acaricides, include, for example, The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K. (2003).


The compounds as described herein can be combined with pharmaceutically acceptable insect growth regulators. Such pharmaceutically acceptable insect growth regulators include, for example, methoprene, pyriproxyfen, tetrahydroazadirachtin, chlorfluazuron, cyromazine, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, ifenuron, tebufenozide, and triflumuron. These compounds tend to provide both initial and sustained treatment of parasite infestations at all stages of insect development, including eggs, on the animal subject, as well as within the environment of the animal subject.


The compounds as described herein can be combined with pharmaceutically acceptable anti-protozoals. Such pharmaceutically acceptable anti-protozoals include, for example, triazintriones like toltrazuril and ponazuril and triazindiones such as clazuril, diclazuril and letrazuril.


In some contemplated embodiments, the compounds are administered with pyridylmethylamine derivatives, such as, for example, pyridylmethylamine derivatives discussed in European Patent Appl. EP0539588 or Int'l Patent Appl. Publ. WO2007/115643.


In some contemplated embodiments, the compounds are administered with nodulisporic acids and derivatives thereof, such as, for example, compounds discussed in U.S. Pat. No. 5,399,582; 5,945,317; 5,962,499; 5,834,260; 6,221,894; or 5,595,991; or WO 1996/29073.


In some contemplated embodiments, the compounds are administered with dihydroazole compounds, such as, for example, compounds discussed in WO 2010/75591.


Other antiparasitic compounds contemplated to be useful in combination therapies with the compounds include, for example, imidazo[1,2-b] pyridazine compounds discussed in US Patent Appl. Publ. No. 2005-0182059; 1-(4-Mono and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanol compounds discussed U.S. Pat. No. 7,361,689; trifluoromethanesulfonanilide oxime ether compounds discussed in U.S. Pat. No. 7,312,248; n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide compounds discussed in US Patent Appl. Publ. 2006-0281695; and 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile compounds discussed in US Appl. Publ. 2006/0128779; isoxazoline compounds discussed in WO Patent Appl, Publ. 2005-085216, WO 2007/026965, WO 2007/070606, WO 2007/075459, WO 2007/079162, WO 2007/105814, WO 2007/125984, WO 2008/019760, WO 2008/122375, WO 2008/150393, WO 2009/002809, WO 2009/003075, WO 2009/022746, WO 2009/035004, WO 2009/045999, WO 2009/051956, WO 2009/035004.


In the contemplated combination therapies, the compounds according to this invention may be administered before, simultaneously, and/or after the other active ingredient(s). In addition, the compounds according to this invention may be administered in the same composition as the other active ingredient(s) and/or in separate compositions from the other active ingredient(s). Further, the compounds according to this invention and other active ingredient(s) may be administered via the same and/or different dosage route.


When the compounds according to this invention are administered in a combination therapy, the weight ratio of the active ingredients may vary widely. Factors influencing this ratio include, for example, the particular compounds; the identity of the other active ingredient(s) be administered in the combination therapy; the dosage route of the compounds and other active ingredient(s); the target condition and pathogen; the type (e.g., species and breed), age, size, sex, diet, activity, and condition of the animal; and pharmacological considerations, such as the activity, efficacy, pharmacokinetic, and toxicology profiles of the compounds and other active ingredient(s). In some contemplated embodiments, for example, the weight ratio of the compounds to the other active ingredient(s) is, for example, is from about 1:3000 to about 3000:1. In some such instances, the weight ratio is from about 1:300 to about 300:1. In other such instances, the weight ratio is from about 1:30 and about 30:1.


In addition to other active ingredients, it is contemplated that the compounds may be administered with one or more other compounds that beneficially affects (e.g., enhances or prolongs) the activity (or other characteristic, such as safety) of the compounds. For example, it is contemplated that the compounds may be administered with one or more synergists, such as, for example, piperonyl butoxide (PBO) and triphenyl phosphate (TPP).


This invention also is directed to kits that are, for example, suitable for use in performing the methods of treatment described above. The kit comprises a therapeutically effective amount of one or more compounds of this invention, and an additional component. The additional component(s) may be, for example, one or more of the following: another ingredient (e.g., an excipient or active ingredient), an apparatus for combining the compound of this invention with another ingredient and/or for administering the compound of this invention, or a diagnostic tool.


The compounds used according to this invention show an excellent activity in treating parasite infestations and in addition are acceptable for the animals treated.


The following table presents suitable compounds of the invention. In case racemate is indicated but only one of the stereoisomer is drawn, also the other stereoisomer is included.


The following compounds are very suitable for use in the method of the invention:














#
Compound
Stereo

















4


embedded image


racemate





51


embedded image


1R, 3R





86


embedded image


1R, 3R





89


embedded image


1R, 3R





197


embedded image


1R, 3R





446


embedded image


1R, 3R





447


embedded image


1R, 3R





449


embedded image


1R, 3R





451


embedded image


1R, 3R





453


embedded image


1R, 3R





454


embedded image


1R, 3R





455


embedded image


1R, 3R





456


embedded image


1R, 3R





460


embedded image


1R, 3R





466


embedded image


1R, 3R









EXAMPLES

The following compounds have been made.


Compounds were synthesized according to methods as described in WO2016168059 and WO2018073127




embedded image


See table 1 on the following page


















TABLE I







#
R2
R3
R4
R12
R13
R14
R15
A1
A2





1
Cl
H
Cl
H
Me
H
H
CH
CH


2
Cl
H
Cl
H
Br
H
H
CH
CH


3
H
Cl
Cl
H
Cl
H
H
CH
CH


4
Cl
H
Cl
H
F
H
H
CH
CH


5
Cl
H
Cl
H
H
F
H
CH
CH


6
Cl
H
Cl
H
Cl
H
H
CF
CF


7
Cl
H
Cl
H
Cl
H
H
CH
CF


8
Cl
H
Cl
H
Cl
H
H
CF
CH


9
Cl
H
Cl
H
Cl
H
H
CF
CH


10
Cl
H
Cl
H
Cl
H
H
CCL
N


11
Cl
H
Cl
H
Cl
H
H
CH
N


12
Cl
H
Cl
H
Cl
H
Me
CH
CF


13
Cl
H
Cl
H
Cl
H
H
C—Me
CH


14
Cl
Cl
Cl
H
Cl
H
H
CF
CH


15
Cl
H
Cl
H
F
H
Me
CH
CF


16
Cl
H
Cl
H
H
F
Me
CH
CH


17
Cl
Cl
H
H
Cl
H
H
CH
CF


18
CF3
H
H
H
Cl
H
Me
CH
CH


19
Cl
H
Cl
H
F
H
H
CF
CH


20
Cl
H
Cl
H
F
H
Me
CF
CH


21
Cl
Cl
Cl
H
F
H
Me
CF
CH


22
Cl
OCF3
H
H
Cl
H
H
CH
CH


23
H
CF3
H
H
Cl
H
H
CH
CH


24
CF3
H
Cl
H
Cl
H
H
CH
CH


25
Cl
H
Cl
H
Cl
H
2,2,2-
CH
CH









Trifluoro-









ethyl


26
Cl
H
Cl
H
Cl
H
n-Propyl
CH
CH


27
Me
H
Cl
H
Cl
H
H
CH
CH


28
Me
H
Cl
H
Cl
H
Me
CH
CH


29
Me
H
Cl
H
Cl
H
H
CF
CH


30
Cl
Cl
Me
H
Cl
H
H
CH
CH


31
H
Cl
F
H
Cl
H
H
CH
CH


32
Br
H
Cl
H
Cl
H
H
CH
CH


33
Br
H
Cl
H
Cl
H
Me
CH
CH


34
Cl
H
Cl
H
Cl
H
H
CH
C—Me


35
Cl
Cl
H
H
Cl
H
H
C—Me
CH


36
Cl
Cl
Cl
H
Cl
H
H
C—Me
CH


37
H
F
Cl
H
Cl
H
H
C—Me
CH


38
Cl
H
Cl
H
Cl
H
Me
C—Me
CH


39
H
F
Cl
H
Cl
H
Me
C—Me
CH


40
Cl
H
Cl
H
Cl
H
H
CH
C—O—Me


41
Cl
H
Cl
H
Cl
H
H
C—Me
C—Me


42
Cl
H
Cl
H
Cl
H
H
CH
C—O—Me


43
Cl
H
Cl
H
Cl
H
H
CH
CF


44
Cl
H
Cl
H
Cl
H
H
CH
C—Me


45
Cl
H
Cl
H
Cl
H
H
CF
CH


46
Cl
H
Cl
H
Cl
H
H
CF
CH


47
Cl
H
Cl
H
Cl
H
H
CH
CCL


48
Cl
H
Cl
H
Cl
H
H
CH
CH


49
Cl
H
Cl
H
Cl
H
H
C—CN
CH


50
Cl
H
Cl
H
Cl
H
H
CF
CF


51
Cl
H
Cl
H
Cl
H
Me
CH
CH


52
Cl
H
Cl
H
Cl
H
H
CH
CF


53
Cl
H
Cl
H
Cl
H
H
N
CH


54
Cl
OMe
Cl
H
Cl
H
H
CF
CH


55
Cl
H
Cl
H
Cl
H
H
CF
CH


56
Cl
H
Cl
H
H
H
H
CF
CH


57
CN
H
Cl
H
Cl
H
H
CF
CH


58
CN
H
Cl
H
Cl
H
Me
CH
CH


59
H
Cl
Cl
H
Cl
H
H
C—CN
CH


60
Cl
Cl
Cl
H
Cl
H
H
C—CN
CH


61
H
F
Cl
H
Cl
H
H
C—CN
CH


62
Cl
H
Cl
H
Cl
H
H
CF
CH


63
Cl
H
Cl
H
Cl
H
H
C—CN
CH


64
Cl
Cl
H
H
Cl
H
H
CH
CH


65
Cl
Cl
H
H
Cl
H
H
CF
CH


66
Cl
H
Cl
H
Cl
H
H
CF
CH


67
Cl
H
Cl
H
Cl
H
H
CH
C—NH2


68
Cl
H
Cl
H
Cl
H
H
N
CF


69
Cl
H
Cl
H
Cl
H
H
N
CH


70
Cl
H
Cl
H
Cl
H
H
N
CH


71
Cl
H
Cl
H
Cl
H
Me
C—CN
CH


72
Cl
Cl
Cl
H
Cl
H
Me
C—CN
CH


73
Cl
H
Cl
H
Cl
H
H
CF
CH


74
Cl
Cl
Cl
H
H
H
H
C—CN
CH


75
Cl
Cl
H
H
H
H
H
C—CN
CH


76
H
Br
Cl
H
Cl
H
H
CH
CH


77
Cl
H
Cl
H
H
H
Me
CH
CH


78
Cl
H
Cl
H
H
H
H
CCL
CH


79
Cl
Cl
Cl
H
Cl
H
H
CH
CH


80
Cl
Cl
Cl
H
Cl
H
H
CF
CH


81
Cl
H
Cl
H
Cl
H
H
N
CH


82
Cl
H
Cl
H
Cl
H
H
C—CN
CH


83
Cl
H
Cl
H
Cl
H
H
C—CN
CH


84
Cl
H
Cl
H
Cl
H
H
C—CN
CH


85
CF3
H
CF3
H
Cl
H
H
C—CN
CH


86
H
Cl
Cl
H
Cl
H
H
N
CH


87
Cl
H
Cl
H
Cl
H
H
CF
C—NH2


88
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH2


89
H
F
Cl
H
Cl
H
H
N
CH


90
Cl
F
H
H
Cl
H
H
CF
C—NH2


91
H
F
Cl
H
Cl
H
H
CF
CH


92
H
Br
Cl
H
Cl
H
H
C—CN
CH


93
H
Cl
Br
H
Cl
H
H
CH
CH


94
CF3
H
H
H
Cl
H
H
C—CN
CH


95
CF3
H
H
H
Cl
H
H
CF
C—NH2


96
CN
H
Cl
H
Cl
H
H
N
CH


97
CN
H
Cl
H
Cl
H
H
CF
C—NH2


98
Cl
H
Cl
H
Cl
H
H
N
CH


99
H
F
F
H
Cl
H
H
CF
CH


100
Br
Br
H
H
Cl
H
H
CF
CH


101
F
CF3
H
H
Cl
H
H
CF
CH


102
Cl
H
Cl
H
Cl
H
H
C—NO2
CH


103
Cl
H
Cl
H
Cl
H
H
CF
CH


104
Cl
H
Cl
H
Cl
H
H
CF
CH


105
F
Br
H
H
Cl
H
H
CF
CH


106
Br
CF3
H
H
Cl
H
H
CF
CH


107
CF3
Br
H
H
Cl
H
H
CF
CH


108
Cl
CF3
H
H
Cl
H
H
CF
CH


109
Cl
H
Cl
H
Cl
H
H
CH
CCL


110
Cl
Cl
H
H
Cl
H
H
CH
CCL


111
Cl
H
Cl
H
Cl
H
H
N
CH


112
Cl
Cl
H
H
Cl
H
H
N
CH


113
CF3
Cl
H
H
Cl
H
H
CF
CH


114
Br
F
H
H
Cl
H
H
CF
CH


115
CF3
F
H
H
Cl
H
H
CF
CH


116
Cl
H
Br
H
Cl
H
H
C—CN
CH


117
Cl
H
Cl
H
Cl
H
H
CH
CF


118
Cl
Cl
Cl
H
Cl
H
H
CH
CF


119
Cl
F
H
H
Cl
H
H
CH
CF


120
H
1-
Cl
H
Cl
H
H
CF
CH




Fluoro-




vinyl


121
H
Cl
1-
H
Cl
H
H
CH
CH





Fluoro-





vinyl


122
Cl
H
1-
H
Cl
H
H
CF
CH





Fluoro-





vinyl


123
Cl
H
1-
H
Cl
H
H
C—CN
CH





Fluoro-





vinyl


124
Cl
H
Cl
H
Cl
H
H
N
CH


125
H
Vinyl
F
H
Cl
H
H
CF
CH


126
H
F
Vinyl
H
Cl
H
H
CF
CH


127
H
Vinyl
CF3
H
Cl
H
H
CF
CH


128
H
CF3
Vinyl
H
Cl
H
H
CF
CH


129
Cl
H
Cl
H
Cl
H
H
N
CH


130
Cl
H
Cl
H
Cl
H
H
N
CH


131
Cl
H
Cl
H
Cl
H
H
CH
N


132
Cl
H
Cl
H
Cl
H
H
CH
N


133
Cl
H
Cl
H
Cl
H
H
N
CF


134
Cl
H
Cl
H
Cl
H
H
N
CF


135
Cl
H
Cl
H
Cl
H
H
CH
N


136
H
Cl
Br
H
Cl
H
H
CF
CH


137
H
Br
Cl
H
Cl
H
H
CF
C—NH2


138
H
Cl
Br
H
Cl
H
H
CF
C—NH2


139
H
Ethynyl
Cl
H
Cl
H
H
C—CN
CH


140
Cl
Cl
Cl
H
Cl
H
H
CF
CH


141
Cl
Cl
Cl
H
Cl
H
H
C—NH2
CF


142
Cl
H
Cl
H
Cl
H
H
C—NH2
CH


143
Cl
Cl
H
H
Cl
H
H
C—NH2
CH


144
H
Cl
Ethynyl
H
Cl
H
H
CH
CH


145
F
Cl
H
H
Cl
H
H
CF
CH


146
F
H
F
H
Cl
H
H
CF
CH


147
F
H
CF3
H
Cl
H
H
CF
CH


148
Cl
H
Cl
H
Cl
H
prop-2-ynyl
CH
CH


149
Cl
F
H
H
Cl
H
prop-2-ynyl
CF
CH


150
Cl
F
H
H
Cl
H
H
C—NH2
CF


151
F
H
Br
H
Cl
H
H
CF
CH


152
Br
H
CF3
H
Cl
H
H
CF
CH


153
Cl
Cl
H
H
Cl
H
H
CF
CH


154
Cl
F
H
H
Cl
H
H
CF
CH


155
Cl
Cl
H
H
Cl
H
H
CH
C—NH2


156
Cl
F
H
H
Cl
H
H
CH
C-NH2


157
F
OMe
F
H
Cl
H
H
CF
CH


158
F
Br
F
H
Cl
H
H
CH
CH


159
F
Br
OMe
H
Cl
H
H
CH
CH


160
F
Br
F
H
Cl
H
H
CF
CH


161
F
Br
OMe
H
Cl
H
H
CF
CH


162
Br
OMe
F
H
Cl
H
H
CF
CH


163
H
F
Cl
H
Cl
H
H
CCL
C—O—Me


164
H
F
Cl
H
Cl
H
H
C—Br
CH


165
Cl
H
Cl
H
Cl
H
H
CCL
N


166
H
F
Cl
H
Cl
H
H
CCL
N


167
Cl
H
Cl
H
Cl
H
H
C—NO2
CH


168
Cl
Cl
H
H
Cl
H
H
C—NO2
CH


169
Cl
Cl
Cl
H
Cl
H
H
C—NO2
CH


170
Cl
F
H
H
Cl
H
H
C—NO2
CH


171
CHF2
Cl
H
H
Cl
H
H
CF
CH


172
CHF2
H
F
H
Cl
H
H
CF
CH


173
CHF2
F
H
H
Cl
H
H
CF
CH


174
F
CHF2
H
H
Cl
H
H
CF
CH


175
Cl
H
Cl
H
Cl
H
H
CF
CH


176
Cl
Cl
H
H
Cl
H
H
CF
CH


177
Cl
Cl
Cl
H
Cl
H
H
CF
CH


178
Cl
F
H
H
Cl
H
H
CF
CH


179
Br
Cl
H
H
Cl
H
H
CF
CH


180
Cl
H
Cl
H
Cl
H
H
C—NH2
CH


181
Cl
Cl
Cl
H
Cl
H
H
C—NH2
CH


182
Cl
F
H
H
Cl
H
H
C—NH2
CH


183
Br
Cl
H
H
Cl
H
H
CF
C—NH2


184
Br
Cl
H
H
Cl
H
H
CF
CH


185
F
F
F
H
Cl
H
H
CF
CH


186
Cl
H
Cl
H
Cl
H
H
CH
C—Br


187
CHF2
H
Cl
H
Cl
H
H
N
CH


188
CHF2
Cl
H
H
Cl
H
H
N
CH


189
CHF2
H
F
H
Cl
H
H
N
CH


190
CHF2
F
H
H
Cl
H
H
N
CH


191
F
CHF2
H
H
Cl
H
H
N
CH


192
H
CHF2
H
H
Cl
H
H
N
CH


193
CHF2
H
Cl
H
Cl
H
Me
CH
CH


194
CHF2
Cl
H
H
Cl
H
Me
CH
CH


195
CHF2
F
H
H
Cl
H
Me
CH
CH


196
F
CHF2
H
H
Cl
H
Me
CH
CH


197
Cl
F
H
H
Cl
H
H
CF
CH


198
H
Cl
F
H
Cl
H
H
CF
CH


199
Br
H
Cl
H
Cl
H
H
CF
C—NH2


200
Cl
Cl
H
H
Cl
H
H
CF
CH


201
Cl
Cl
H
H
Cl
H
H
C—NH2
CF


202
Cl
Cl
H
H
Cl
H
H
CH
CF


203
Cl
F
H
H
Cl
H
H
CF
CH


204
Cl
H
Cl
H
Cl
H
H
CH
C—NH2


205
Cl
H
Cl
H
Cl
H
H
CF
C—NH2


206
Cl
Cl
H
H
Cl
H
H
C—NH2
CH


207
Cl
H
Cl
H
Cl
H
H
CF
C—NH2


208
CF3
F
H
F
Cl
H
H
CF
C—NH—CO—CF3


209
Cl
F
H
Me
F
H
H
CF
C—NH2


210
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH2


211
Cl
H
Cl
H
Cl
H
H
C—Br
CH


212
Cl
F
H
F
F
H
H
CH
CH


213
H
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CH2—O—Me


214
Cl
Cl
Cl
F
Cl
H
H
CF
C—NH—CO—CHF2


215
F
H
CF3
H
Cl
H
H
CF
C—NH2


216
Cl
F
H
H
Cl
H
H
CF
CH


217
Cl
H
Cl
H
Cl
H
H
CF
CH


218
Cl
H
Cl
H
Cl
H
H
CF
C—NH—CO—CHF2


219
Cl
H
Cl
H
Cl
H
Et
C—CN
CH


220
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CHF2


221
Cl
F
H
F
Cl
H
H
CF
C—NH2


222
Cl
F
H
Me
Cl
H
H
CH
CH


223
H
Cl
CF3
H
Cl
H
H
CF
C—NH2


224
Cl
Cl
H
H
Cl
H
H
CF
CH


225
H
I
H
H
Cl
H
H
CF
CH


226
F
Cl
Cl
H
Cl
H
H
CF
C—NH2


227
Cl
F
H
F
F
H
H
CF
CH


228
Cl
H
Cl
H
Cl
H
H
CF
C—NH—CO—CHF2


229
CF3
F
H
F
Cl
H
H
CF
C—NH—CO—CHF2


230
Cl
F
H
Me
Cl
H
H
CF
CH


231
Cl
F
H
Cl
Me
H
H
CH
CH


232
Cl
F
H
Cl
Me
H
H
CF
C—NH2


233
SF5
H
Cl
H
Cl
H
H
CF
CH


234
Cl
F
H
CF3
Cl
H
H
CH
CH


235
Br
H
SF5
H
Cl
H
H
CF
C—NH2


236
Cl
H
Cl
F
Cl
H
H
CF
C—NH—CO—CHF2


237
Cl
Cl
H
F
Cl
H
H
CF
C—NH—CO—CF3


238
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CHF2


239
Cl
H
Cl
H
Cl
H
H
CCL
C—NH—CO—Me


240
Cl
F
H
Cl
Me
H
H
CF
CH


241
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO-Phenyl


242
Cl
H
Cl
H
Cl
H
H
CF
C—CO—O—ME


243
CF3
F
H
H
Cl
H
Me
CF
C—NH2


244
I
H
H
H
Cl
H
H
CF
CH


245
I
H
H
H
Cl
H
H
CF
C—NH2


246
CF3
H
Br
H
Cl
H
H
CF
C—NH2


247
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CHF2


248
Cl
F
Cl
H
Cl
H
H
CF
CH


249
Cl
Cl
H
H
Cl
H
H
CF
C—NMe—CO—CHF2


250
Cl
F
Cl
H
Cl
H
H
CF
C—NH2


251
F
Cl
CF3
H
Cl
H
H
CF
CH


252
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CHF2


253
CF3
F
H
H
Cl
H
prop-2-ynyl
CF
C—NH2


254
OCHF2
H
Cl
H
Cl
H
H
CF
CH


255
Cl
H
Cl
H
Cl
H
H
CF
C—Br


256
Cl
H
Cl
F
Cl
H
H
CF
C—NH—CO—CF3


257
SF5
H
Cl
H
Cl
H
H
CF
C—NH2


258
Cl
Cl
H
F
Cl
H
H
CF
C—NH—CO—CHF2


259
Cl
H
Cl
H
Cl
H
H
CF
CH


260
Cl
F
H
H
Cl
H
H
CF
C—NH2


261
Cl
Cl
CF3
H
Cl
H
H
CF
C—NH2


262
H
F
CF3
H
Cl
H
H
CF
C—NH—CO—CBrF2


263
Cl
Cl
Br
H
Cl
H
H
CF
CH


264
Cl
F
H
Me
F
H
H
CF
CH


265
Cl
F
H
F
Cl
H
H
CH
CH


266
Cl
Cl
CF3
H
Cl
H
H
CF
CH


267
H
F
CF3
H
Cl
H
H
CF
C—NH—CO—CClF2


268
Cl
Cl
H
H
Cl
H
H
CF
CH


269
Cl
F
H
H
Cl
H
H
CF
CH


270
SF5
H
H
H
Cl
H
H
CF
CH


271
H
I
H
H
Cl
H
H
CF
C—NH2


272
CHF2
H
Cl
H
Cl
H
H
CF
C—NH2


273
F
Cl
CF3
H
Cl
H
H
CF
C—NH2


274
Cl
F
H
F
Cl
H
H
CF
C—NH—CO—CF3


275
Cl
Cl
H
H
Cl
H
H
CF
C—NH2


276
Cl
H
Cl
H
Cl
H
H
C—Br
CH


277
SF5
H
H
H
Cl
H
H
CF
C—NH2


278
H
F
CF3
H
Cl
H
H
CF
C—NH2


279
Cl
Cl
H
H
Cl
H
H
CF
CH


280
H
Br
CF3
H
Cl
H
H
CF
C—NH2


281
CHF2
F
H
H
Cl
H
H
CF
C—NH2


282
F
F
F
H
Cl
H
H
CF
C—NH2


283
F
Cl
Cl
H
Cl
H
H
CF
CH


284
H
CF3
F
H
Cl
H
H
CF
C—NH—CO—CF3


285
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CCl3


286
Cl
H
Cl
H
Cl
H
H
CF
C—O—Me


287
Cl
H
CF3
H
Cl
H
H
CF
CH


288
Cl
F
H
Me
Cl
H
H
CF
C—NH2


289
Cl
F
H
H
F
F
H
CH
CH


290
Cl
Cl
H
H
Cl
H
H
C—NH—CO—CHF2
CH


291
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CClF2


292
F
F
F
H
Cl
H
H
CF
CH


293
Cl
H
Cl
H
Cl
H
H
CH
C—Br


294
H
H
CF3
H
Cl
H
H
CF
CH


295
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CHCl2


296
Cl
H
Cl
H
Cl
H
H
CF
CH


297
Cl
H
Cl
H
Cl
H
H
C—CF═CH2
CH


298
Cl
H
Cl
H
Cl
H
H
CF
CH


299
Cl
H
Cl
H
Cl
H
H
CF
C—CH═CH2


300
Cl
H
Cl
H
Cl
H
H
C—CH═CH2
CH


301
H
F
CF3
H
Cl
H
H
CF
C—NH—CO—CHCl2


302
Me
F
CF3
H
Cl
H
H
CF
CH


303
Me
F
CF3
H
Cl
H
H
CF
C—NH2


304
CHF2
Cl
H
H
Cl
H
H
CF
C—NH2


305
H
F
CF3
H
Cl
H
H
CF
C—NH2


306
Cl
Br
Cl
H
Cl
H
H
CF
CH


307
Cl
Cl
Br
H
Cl
H
H
CH
CH


308
Cl
Cl
H
H
Cl
H
Me
CF
C—NH2


309
H
F
Br
H
Cl
H
H
CF
C—NH2


310
Cl
F
H
F
Cl
H
H
CF
CH


311
F
H
Br
H
Cl
H
H
CF
C—NH2


312
Cl
Cl
Br
H
Cl
H
H
CF
C—NH2


313
Cl
F
H
Me
F
H
H
CH
CH


314
Cl
H
Cl
H
Cl
H
H
CF
CH


315
Cl
F
H
F
Me
H
H
CH
CH


316
Cl
H
Cl
H
Cl
H
H
CF
CH


317
Cl
H
Cl
H
Cl
H
H
CH
C—Br


318
Cl
H
Cl
H
Cl
H
H
CF
CH


319
Cl
Cl
Cl
F
Cl
H
H
CF
C—NH—CO—CF3


320
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CF2—Me


321
Cl
F
H
Cl
F
H
H
CH
CH


322
F
F
Br
H
Cl
H
H
CF
C—NH2


323
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CHF2


324
Cl
H
Cl
H
Cl
H
H
C—CF═CH2
CH


325
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CH2—O—CF3


326
CF3
Cl
H
H
Cl
H
H
CF
C—NH—CO—CF3


327
Cl
Cl
Cl
H
Cl
H
H
CF
CH


328
Cl
H
Cl
F
Cl
H
H
CF
CH


329
H
F
Cl
H
Cl
H
H
CH
C—NH2


330
H
Cl
Cl
Me
Cl
H
H
CF
C—NH—CO—CHF2


331
Cl
F
H
H
Cl
H
H
CF
C—NMe—CO—CHF2


332
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CH2—O—CF3


333
CF3
F
H
H
F
H
H
CF
C—NH—CO—CF3


334
CF3
F
H
H
Cl
H
H
CF
CH


335
F
H
CF3
H
Cl
H
H
CF
C—NH2


336
Cl
Cl
Cl
H
Cl
H
H
CF
C—NMe—CO—CHF2


337
CF3
F
H
F
F
H
H
CF
C—NH—CO—CF3


338
H
F
CF3
H
Cl
H
H
CF
C—Me


339
CF3
F
H
H
F
H
H
CF
C—NH—CO—CHF2


340
Br
Cl
H
H
Cl
H
H
CF
C—NH—CO—CHF2


341
Cl
Cl
H
H
Cl
H
Me
CF
C—NH—CO—CH2—O—CF3


342
Cl
H
Cl
H
Cl
H
H
CF
C—NMe—CO—CHF2


343
Cl
Cl
H
H
F
H
H
CF
CH


344
CF3
F
H
F
Cl
H
H
CF
CH


345
Cl
Cl
H
H
F
H
H
CF
C—NH—CO—CHF2


346
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CH(Me)—O—C2H5


347
Cl
F
H
H
Cl
H
H
CH
C—NH—CO—CF3


348
Cl
Cl
H
F
F
H
H
CF
C—NH—CO—CHF2


349
Cl
Cl
Cl
H
F
H
H
CF
C—NH—CO—CF3


350
H
F
Cl
H
Cl
F
H
CH
CH


351
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO-











tetrahydrofuran-2-yl


352
Cl
Cl
H
F
F
H
H
CF
C—NH—CO—CF3


353
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CH(Me)—O—CF3


354
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CH2-cProp


355
H
F
CF3
H
Cl
H
H
CF
C—NH—CO—CHF2


356
H
Cl
H
H
Cl
H
H
CF
C—NH2


357
CF3
F
H
H
F
H
H
CF
C—NH—CO—CF3


358
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—C2H5


359
H
F
H
H
Cl
H
H
CF
C—NH—CO—CHF2


360
H
F
CF3
H
Cl
H
H
CF
C—NH2


361
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CH(Me)—O—CH2H5


362
H
F
CF3
H
Cl
H
H
CF
CH


363
F
H
CF3
H
Cl
H
H
CF
C—NH—CO-











tetrahydrofuran-2-yl


364
Cl
H
Cl
F
F
H
H
CF
C—NH—CO—CHF2


365
H
Cl
H
H
Cl
H
H
CF
C—NH—CO—CHF2


366
Cl
F
H
F
Cl
H
H
CF
CH


367
H
F
Br
H
Cl
H
H
CF
C—NH—CO—CH(Me)—O—CF3


368
Cl
Cl
H
H
Cl
H
H
CF
C—NMe—CO—CF3


369
Cl
F
H
H
Cl
H
H
CF
C—NH—CO-











tetrahydrofuran-2-yl


370
Cl
Cl
H
H
Cl
H
H
CH
C—NH—CO—CF3


371
CF3
Cl
H
H
Cl
H
H
CF
C—NH—CO—CHF2


372
Cl
Cl
H
H
F
H
H
CF
CH


373
Cl
H
Cl
F
Cl
H
H
CF
CH


374
Cl
Cl
H
H
F
H
H
CF
C—NH—CO—CHF2


375
Cl
F
H
F
Cl
H
H
CF
CH


376
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CH2—CH═CH2


377
H
H
F
H
Cl
H
H
CF
C—NH2


378
Cl
Cl
H
F
Cl
H
H
CF
CH


379
Cl
Cl
H
H
F
H
H
CF
C—NH—CO—CF3


380
H
Cl
Br
H
Cl
H
H
CF
C—NH—CO—CF3


381
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—CHF2


382
H
F
CF3
H
Cl
H
H
C—Me
C—NH2


383
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—C2H4—O—C2H5


384
Cl
Cl
Cl
F
F
H
H
CF
C—NH—CO—CF3


385
F
H
CF3
H

3

H
H
CF
C—NH—CO—CH2—CH═CH2


386
H
H
CF3
H
Cl
H
H
CF
C—NH2


387
H
Cl
Cl
Me
Cl
H
H
CF
C—NH—CO—CF3


388
Cl
Cl
Cl
H
F
H
H
CF
C—NH—CO—CHF2


389
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—C3H7


390
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CClF2


391
CF3
F
H
F
F
H
H
CF
CH


392
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—C2H5


393
H
F
Br
H
Cl
H
H
CF
C—NH—CO—CH2—O—CF3


394
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CH2—O—Me


395
Cl
Cl
Cl
H
F
H
H
CF
CH


396
Cl
Cl
Cl
H
Cl
H
H
CF
CH


397
CF3
F
H
F
F
H
H
CF
CH


398
H
H
CF3
H
Cl
H
H
CF
C—NH—CO-











tetrahydrofuran-2-yl


399
F
H
CF3
H
Cl
H
H
CF
C—NH—CO—C2H5


400
Cl
Cl
Cl
H
F
H
H
CF
CH


401
F
H
CF3
H
Cl
H
H
CF
C—NH—CO—CF2CHF2


402
Cl
Cl
H
H
Cl
H
Me
CF
C—NH—CO—CF3


403
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—Me


404
H
F
Cl
H
Cl
H
H
CH
C—NH—CO—CF3


405
Cl
H
Cl
H
Cl
H
H
CH
C—NH—CO—CF3


406
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—Me


407
Cl
Cl
H
F
F
H
H
CF
CH


408
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CF3


409
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—CH2—CH═CH2


410
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CH2—O—CH2—CF3


411
Cl
Cl
Cl
F
F
H
H
CF
CH


412
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CH2-cProp


413
F
H
CF3
H
Cl
H
H
CF
C—NH—CO—CHF2


414
H
F
CF3
Me
Cl
H
H
CF
C—NH—CO—CF3


415
Cl
Cl
Cl
H
Cl
H
H
CF
C—NH—CO—CF2CHF2


416
CF3
F
H
H
F
H
H
CF
CH


417
CF3
F
H
H
Cl
H
H
CH
C—NH—CO—CF3


418
Cl
Cl
H
H
Cl
H
Me
CF
C—NH—CO—CH(Me)—O—C2H5


419
H
Br
H
H
Cl
H
H
CF
C—NH2


420
H
Cl
Cl
Me
Cl
H
H
CF
C—NH—CO—CF3


421
CF3
F
H
F
F
H
H
CF
C—NH—CO—CHF2


422
CF3
Cl
H
H
Cl
H
H
CF
C—NH—CO—CClF2


423
Cl
Cl
H
H
Cl
H
H
CF
C—NH—Me


424
Cl
Cl
H
H
F
H
H
CF
C—NH—CO—CF3


425
Cl
Cl
H
F
F
H
H
CF
CH


426
Cl
Cl
Cl
H
F
H
H
CF
CH


427
Cl
Cl
Cl
F
F
H
H
CF
CH


428
Cl
Cl
Cl
H
Cl
H
H
CF
CH


429
H
F
CF3
H
Cl
H
H
CF
CH


430
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—CF2CHF2


431
CF3
F
H
F
Cl
H
H
CF
CH


432
C
F
H
H
Cl
H
H
CF
C—NH—CO—CF2CHF2


433
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—C2H5


434
Cl
Cl
H
H
Cl
H
H
CF
C—NH—CO—CF2CHF2


435
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—CClF2


436
H
F
Br
H
Cl
H
H
CF
C—NH—CO—CH2—CH═CH2


437
CF3
F
H
H
F
H
H
CF
CH


438
H
F
CF3
H
Cl
H
H
CF
CF


439
H
F
CF3
Me
Cl
H
H
CF
CH


440
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—CH2—O—CF3


441
H
H
CF3
H
Cl
H
H
CF
C—NH—CO—CH(Me)—O—CF3


442
Cl
F
H
H
Cl
H
H
CF
C—NH—CO—C2F5


443
H
F
CF3
H
Cl
H
H
CF
C—NH—CO—CF2—CHF2


444
Cl
Cl
H
F
F
H
H
CF
CH


445
CF3
F
H
H
F
H
H
CF
C—NH—CO—CHF2


446
Cl
H
Cl
H
F
H
H
CH
CH


447
Cl
H
Cl
H
F
H
H
CF
CH


448
Cl
H
Cl
H
F
H
H
CF
CH


449
Cl
H
Cl
H
Cl
H
H
CF
CH


450
Cl
H
Cl
H
Cl
H
H
CF
CH


451
F
F
F
H
Cl
H
H
CF
CH


452
F
F
H
H
Cl
H
H
CF
CH


453
Cl
H
Cl
H
Cl
H
H
N
CH


454
Cl
H
Cl
H
Cl
H
H
N
CH


455
Cl
H
Cl
H
Cl
H
H
CH
N


456
Cl
H
Cl
H
Cl
H
H
CF
N


457
Cl
H
Cl
F
Me
H
H
N
CH


458
Cl
H
Cl
H
Cl
H
H
CF
CH


460
Cl
H
Cl
H
Cl
H
H
N
CH


462
Cl
Cl
H
H
Cl
H
H
N
CH


463
Cl
H
Cl
H
F
H
H
N
CH


464
Cl
H
Cl
F
Cl
H
H
N
CH


465
Cl
H
Cl
H
H
F
H
N
CH


466
Cl
Cl
Cl
H
Cl
H
H
CH
N


467
Cl
H
Cl
H
Cl
F
H
N
CH


468
H
Cl
Cl
H
Me
F
H
N
CH


469
Cl
F
Cl
H
Cl
H
H
N
CH


470
Cl
Cl
Cl
H
Cl
H
H
N
CH


471
CF3
H
CF3
H
Cl
H
H
N
CH


472
CF3
H
CF3
H
Cl
H
H
CF
CH


473
CF3
H
CF3
H
F
H
H
CF
CH


474
CF3
H
CF3
F
F
H
H
N
CH


475
Cl
H
CF3
H
Cl
H
H
N
CH


476
Cl
H
CF3
H
Cl
H
H
N
CH


477
Cl
H
Cl
F
F
H
H
N
CH


478
F
F
F
H
Cl
H
H
N
CH


479
F
F
F
H
F
H
H
N
CH


480
Cl
H
Cl
H
F
F
H
N
CH















#
A3
A4
A5







1
CF
CH
CH



2
CF
CH
CH



3
CF
CH
CH



4
CF
CH
CH



5
CF
CH
CH



6
CH
CH
CH



7
CF
CH
CH



8
CF
CH
CF



9
CH
CH
CF



10
CH
CH
CH



11
CCL
CH
CH



12
CH
CH
CH



13
CF
CH
CH



14
CF
CH
CH



15
CH
CH
CH



16
CF
CH
CH



17
CH
CH
CH



18
CF
CH
CH



19
CF
CH
CH



20
CF
CH
CH



21
CF
CH
CH



22
CF
CH
CH



23
CF
CH
CH



24
CF
CH
CH



25
CF
CH
CH



26
CF
CH
CH



27
CF
CH
CH



28
CF
CH
CH



29
CH
CH
CF



30
CF
CH
CH



31
CF
CH
CH



32
CF
CH
CH



33
CF
CH
CH



34
CF
CH
CH



35
CF
CH
CH



36
CF
CH
CH



37
CF
CH
CH



38
CF
CH
CH



39
CF
CH
CH



40
CF
CH
CH



41
CF
CH
CH



42
CCL
CH
CH



43
C—Br
CH
CH



44
CCL
CH
CH



45
CH
CF
CH



46
CCL
CH
CH



47
C—Me
CH
CH



48
CF
CH
CH



49
CF
CH
CH



50
CF
CH
CH



51
CF
CH
CH



52
C—NH—Me
CH
CH



53
CCL
CH
CH



54
CF
CH
CH



55
CF
CH
CH



56
CF
CH
CH



57
CF
CH
CH



58
CF
CH
CH



59
CF
CH
CH



60
CF
CH
CH



61
CF
CH
CH



62
C—I
CH
CH



63
CF
CH
CH



64
CF
CH
CH



65
CF
CH
CH



66
C—NH—Me
CH
CH



67
CF
CH
CH



68
CH
CH
CH



69
CF
CH
CF



70
CF
CH
C—Me



71
CF
CH
CH



72
CF
CH
CH



73
C—CO—Me
CH
CH



74
CF
CH
CH



75
CF
CH
CH



76
CF
CH
CH



77
CF
CH
CH



78
CF
CH
CH



79
CF
CH
CH



80
CF
CH
CH



81
CF
C—Me
CH



82
C—Me
CH
CF



83
CCL
CH
CH



84
CH
C—Br
CH



85
CF
CH
CH



86
CF
CH
CF



87
CF
CH
CH



88
CF
CH
CH



89
CF
CH
CF



90
CF
CH
CH



91
CF
CH
CH



92
CF
CH
CH



93
CF
CH
CH



94
CF
CH
CH



95
CF
CH
CH



96
CF
CH
CF



97
CF
CH
CH



98
CF
C—NH2
CF



99
CF
CH
CH



100
CF
CH
CH



101
CF
CH
CH



102
CF
CH
CH



103
CF
C—NH2
CH











104
C—NH—CH═CH—C
CH












105
CF
CH
CH



106
CF
CH
CH



107
CF
CH
CH



108
CF
CH
CH



109
N
CH
CH



110
N
CH
CH



111
CF
C—NH2
CF



112
CF
C—NH2
CF



113
CF
CH
CH



114
CF
CH
CH



115
CF
CH
CH



116
CF
CH
CH



117
C—NH2
CF
CH



118
C—NH2
CF
CH



119
C—NH2
CF
CH



120
CF
CH
CH



121
CF
CH
CH



122
CF
CH
CH



123
CF
CH
CH



124
CF
C—I
CF



125
CF
CH
CH



126
CF
CH
CH



127
CF
CH
CH



128
CF
CH
CH



129
CF
C—CH═CH2
CF



130
CF
C—CFCH2
CF



131
CF
C—Br
CH



132
CF
C—Me
CH



133
C—CH═CH2
CH
CH



134
C—CF═CH2
CH
CH



135
CF
C—CH═CH2
CH



136
CF
CH
CH



137
CF
CH
CH



138
CF
CH
CH



139
CF
CH
CH



140
CF
C—NH2
CH



141
CH
CF
CH



142
CF
CH
CF



143
CF
CH
CF



144
CF
CH
CH



145
CF
CH
CH



146
CF
CH
CH



147
CF
CH
CH



148
CF
CH
CH



149
CF
CH
CH



150
CH
CF
CH



151
CF
CH
CH



152
CF
CH
CH



153
CH
C—NH2
CH



154
CH
C—NH2
CH



155
CH
CF
CH



156
CH
CF
CH



157
CF
CH
CH



158
CF
CH
CH



159
CF
CH
CH



160
CF
CH
CH



161
CF
CH
CH



162
CF
CH
CH



163
N
CH
CH



164
N
C—O—Me
CH



165
C—O—Me
CH
CH



166
C—O—Me
CH
CH



167
CF
CH
CH



168
CF
CH
CH



169
CF
CH
CH



170
CF
CH
CH



171
CF
CH
CH



172
CF
CH
CH



173
CF
CH
CH



174
CF
CH
CH



175
C—NH2
CF
CH



176
C—NH2
CF
CH



177
C—NH2
CF
CH



178
C—NH2
CF
CH



179
CF
CH
CH



180
CF
CH
CH



181
CF
CH
CH



182
CF
CH
CH



183
CF
CH
CH



184
CF
C—NH2
CH



185
CF
CH
CH



186
CF
CF
CH



187
CF
CH
CF



188
CF
CH
CF



189
CF
CH
CF



190
CF
CH
CF



191
CF
CH
CF



192
CF
CH
CF



193
CF
CH
CH



194
CF
CH
CH



195
CF
CH
CH



196
CF
CH
CH



197
CF
CH
CH



198
CH
CH
CF



199
CF
CH
CH



200
CF
C—NH2
CH



201
CH
CF
CH



202
C—NH2
CF
CH



203
CF
C—NH2
CH



204
CH
CF
CH



205
CH
CH
CH



206
CF
CH
CH



207
CF
CH
CH



208
CF
CH
CH



209
CF
CH
CH



210
CH
CH
CF



211
CF
CH
CF



212
CF
CH
CH



213
CF
CH
CH



214
CF
CH
CH



215
CF
CH
CH



216
CF
CH
CH



217
CF
C—Br
CH



218
CH
CH
CF



219
CF
CH
CH



220
CF
CH
CH



221
CF
CH
CH



222
CF
CH
CH



223
CF
CH
CH



224
CF
C—NH—CO—CF3
CH



225
CF
CH
CH



226
CF
CH
CH



227
CF
CH
CH



228
CF
CH
CH



229
CF
CH
CH



230
CF
CH
CH



231
CF
CH
CH



232
CF
CH
CH



233
CF
CH
CH



234
CF
CH
CH



235
CF
CH
CH



236
CF
CH
CH



237
CF
CH
CH



238
CH
CH
CF



239
CF
CH
CH



240
CF
CH
CH



241
CF
CH
CH



242
CF
CH
CH



243
CF
CH
CH



244
CF
CH
CH



245
CF
CH
CH



246
CF
CH
CH



247
CH
CH
CF



248
CF
CH
CH



249
CF
CH
CH



250
CF
CH
CH



251
CF
CH
CH



252
CF
CH
CH



253
CF
CH
CH



254
CF
CH
CH



255
CF
CH
CH



256
CF
CH
CH



257
CF
CH
CH



258
CF
CH
CH



259
C—NH2
CH
CF



260
CH
CH
CF



261
CF
CH
CH



262
CF
CH
CH



263
CF
CH
CH



264
CF
CH
CH



265
CF
CH
CH



266
CF
CH
CH



267
CF
CH
CH



268
C—NH—CO—CF3
CH
CF



269
C—NH2
CH
CF



270
CF
CH
CH



271
CF
CH
CH



272
CF
CH
CH



273
CF
CH
CH



274
CF
CH
CH



275
CH
CH
CF



276
CF
CH
CH



277
CF
CH
CH



278
CF
CH
CH



279
CF
C—NH—CO—CClF2
CH



280
CF
CH
CH



281
CF
CH
CH



282
CF
CH
CH



283
CF
CH
CH



284
CF
CH
CH



285
CF
CH
CH



286
CF
CH
CH



287
CF
CH
CH



288
CF
CH
CH



289
CF
CH
CH



290
CF
CH
CH



291
CF
CH
CH



292
CF
CH
CH



293
CF
CH
CH



294
CF
CH
CH



295
CF
CH
CH



296
CF
C—CH═CH2
CH



297
CF
CH
CF



298
C—CH═CH2
CH
CH



299
CF
CH
CH



300
CF
CH
CH



301
CF
CH
CH



302
CF
CH
CH



303
CF
CH
CH



304
CF
CH
CH



305
CF
CH
CH



306
CF
CH
CH



307
CF
CH
CH



308
CF
CH
CH



309
CF
CH
CH



310
CF
CH
CH



311
CF
CH
CH



312
CF
CH
CH



313
CF
CH
CH



314
C—Br
CH
CH



315
CF
CH
CH



316
C—CF═CH2
CH
CH



317
CF
CF
CH



318
CF
CH
C—CH═CH2



319
CF
CH
CH



320
CF
CH
CH



321
CF
CH
CH



322
CF
CH
CH



323
CH
CH
CF



324
CF
CH
CH



325
CF
CH
CH



326
CF
CH
CH



327
CF
C—NH—CO—CF3
CH



328
CF
C—NH—CO—CHF2
CH



329
CCL
CH
CH



330
CF
CH
CH



331
CF
CH
CH



332
CF
CH
CH



333
CF
CH
CH



334
CF
C—NH—CO—CF2—CHF2
CH



335
CF
CH
CH



336
CF
CH
CH



337
CF
CH
CH



338
CF
C—NH2
CH



339
CF
CH
CH



340
CF
CH
CH



341
CF
CH
CH



342
CF
CH
CH



343
CF
C—NH—CO—CF3
CH



344
CF
C—NH—CO—CF3
CH



345
CF
CH
CH



346
CF
CH
CH



347
CF
CH
CH



348
CF
CH
CH



349
CF
CH
CH



350
CF
CH
CH



351
CF
CH
CH



352
CF
CH
CH



353
CF
CH
CH



354
CF
CH
CH



355
CH
CH
CF



356
CF
CH
CH



357
CH
CH
CF



358
CF
CH
CH



359
CF
CH
CH



360
CH
CH
CF



361
CF
CH
CH



362
CF
C—NH—CO—CF3
CH



363
CF
CH
CH



364
CF
CH
CH



365
CF
CH
CH



366
CF
C—NH—CO—CHF2
CH



367
CF
CH
CH



368
CF
CH
CH



369
CF
CH
CH



370
CF
CH
CH



371
CF
CH
CH



372
CF
C—NH—CO—CHF2
CH



373
CF
C—NH—CO—CF3
CH



374
CH
CH
CF



375
CF
C—NH—CO—CF3
CH



376
CF
CH
CH



377
CF
CH
CH



378
CF
C—NH—CO—CHF2
CH



379
CF
CH
CH



380
CF
CH
CH



381
CF
CH
CH



382
C—Br
CH
CH



383
CF
CH
CH



384
CF
CH
CH



385
CF
CH
CH



386
CF
CH
CH



387
CH
CH
CF



388
CF
CH
CH



389
CF
CH
CH



390
CF
CH
CH



391
CF
C—NH—CO—CHF2
CH



392
CF
CH
CH



393
CF
CH
CH



394
CF
CH
CH



395
CF
C—NH—CO—CHF2
CH



396
CF
C—NH—CO—CHF2
CH



397
CF
C—NH—CO—CF3
CH



398
CF
CH
CH



399
CF
CH
CH



400
CF
C—NH—CO—Me
CH



401
CF
CH
CH



402
CF
CH
CH



403
CF
CH
CH



404
CCL
CH
CH



405
CF
CH
CH



406
CF
CH
CH



407
CF
C—NH—CO—CF3
CH



408
CF
CH
CH



409
CF
CH
CH



410
CF
CH
CH



411
CF
C—NH—CO—CHF2
CH



412
CF
CH
CH



413
CF
CH
CH



414
CH
CH
CF



415
CF
CH
CH



416
CF
C—NH—CO—CF3
CH



417
CF
CH
CH



418
CF
CH
CH



419
CF
CH
CH



420
CF
CH
CH



421
CF
CH
CH



422
CF
CH
CH



423
CF
CH
CH



424
CH
CH
CF



425
CF
C—NH—CO—CHF2
CH



426
CF
C—NH—CO—CF3
CH



427
CF
C—NH—CO—CF3
CH



428
CF
C—NH—CO—CF2—CF2H
CH



429
CF
C—NH—CO—CHF2
CH



430
CF
CH
CH



431
CF
C—NH—CO—CHF2
CH



432
CF
CH
CH



433
CF
CH
CH



434
CF
CH
CH



435
CF
CH
CH



436
CF
CH
CH



437
CF
C—NH—CO—CHF2
CH



438
CF
C—NH—CO—CHF2
CH



439
CF
C—NH—CO—CF3
CH



440
CF
CH
CH



441
CF
CH
CH



442
CF
CH
CH



443
CH
CH
CF



444
CF
C—NH—CO—Me
CH



445
CH
CH
CF



446
CF
CH
CH



447
CF
CH
CH



448
CF
CH
CH



449
CF
CH
CF



450
CF
CH
CF



451
CF
CH
CH



452
CF
CH
CH



453
CF
CH
CF



454
CF
C—Me
CH



455
CF
CH
CF



456
CH
CH
CF



457
CF
CH
CF



458
CH
CH
CF



460
CF
CH
N



462
CF
CH
CF



463
CF
CH
CF



464
CF
CH
CF



465
CF
CH
CF



466
CF
CH
CF



467
CF
CH
CF



468
CF
CH
CF



469
CF
CH
CF



470
CF
CH
CF



471
CF
CH
CF



472
CF
CH
CH



473
CF
CH
CH



474
CF
CH
CF



475
CF
CH
CF



476
CF
CH
CF



477
CF
CH
CF



478
CF
CH
CF



479
CF
CH
CF



480
CF
CH
CF










Structures of the compounds 1-480 are presented in FIG. 4. In case racemate is indicated but only one of the stereoisomer is drawn, also the other stereoisomer is intended.


In Vitro Assays—Ectoparasites
Example 1: Tick Larvae Contact Assay

Tick larvae (Rhipicephalus microplus) were immersed for approximately 3 minutes in declining concentrations of a test compound (dissolved in a DMSO-emulsifier-deionized water mixture). Tick inhibition (% of damage+dead ticks per test concentration) was assessed approximately 24 hours after contact exposure. The vitality of used parasites was confirmed in negative control groups (i.e. an untreated control and a solvent control).


Results: Compounds with activity of 80% inhibition at test concentration of 388 μM are active.


(*indicates compounds with activity of 80% inhibition at test concentration of 49 μM)


Compounds 1, 3*, 5*, 6*, 7, 8*, 9, 10, 11, 12, 13*, 14*, 15*, 16*, 17, 18*, 19*, 20*, 21, 22, 23*, 24, 25, 26*, 27, 28, 30*, 35*, 39*, 50*, 51*, 55*, 59*, 61*, 63*, 64*, 65*, 80*, 87*, 88*, 89*, 90*, 91*, 92, 94, 95*, 99*, 101*, 107*, 113*, 114*, 115*, 117, 120, 126*, 136*, 137*, 140, 145*, 147*, 151, 152, 160*, 165*, 168*, 170*, 173*, 179*, 183*, 185*, 197*, 199*, 201, 203* and 207*.


Compounds with tick activity of ≥80% inhibition at test concentration of 25 μM are active, i.e.:


Compounds 4, 19, 37, 51, 55, 56, 59, 63, 64, 65, 80, 87, 90, 91, 95, 99, 100, 114, 136, 145, 147, 149, 150, 160, 170, 173, 179, 185, 197, 209, 212, 215, 216, 221, 225, 227, 230, 252, 264, 265, 278, 281, 283, 284, 289, 292, 294, 302, 309, 310, 313, 321, 331, 333, 335, 352, 376, 379, 386, 423 and 432.


Compounds with tick activity of 80% inhibition at test concentration of 100 ppm are active, i.e.:


Compounds 1, 2, 3, 4, 5, 6, 7, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 35, 37, 46, 49, 50, 51, 55, 56, 59, 63, 64, 65, 69, 80, 81, 86, 87, 88, 89, 90, 91, 95, 99, 100, 101, 107, 113, 114, 115, 126, 136, 145, 147, 149, 150, 160, 169, 171, 173, 179, 183, 184, 185, 197, 200, 203, 209, 212, 213, 215, 216, 220, 221, 223, 225, 227, 230, 233, 252, 264, 265, 278, 281, 283, 284, 289, 292, 294, 302, 309, 310, 313, 321, 331, 335, 352, 376, 379, 386, 423, 432, 469, 470, 471, 472, 473, 474, 475, 477, 478, 479, and 480.


Example 2: Flea Contact Assay

Adult fleas (Ctenocephalides felis) were exposed to filter paper impregnated with declining concentrations of a test compound (dissolved in a DMSO-emulsifier-deionized water mixture). After approximately 48 hours of continuous contact exposure, flea inhibition (% of dead+damaged fleas per test concentration) was assessed. The vitality of used parasites was confirmed in negative control groups (i.e., an untreated control and a solvent control).


Results: Compounds with flea activity of 80% inhibition at test concentration of 1000 ppm are active, i.e.: Compounds 55, 65, 90, 91, 99, 100, 114, 115, 145, 147, 179, 185, 197 289, 469, 470, 471, 472, 473, 474, 477, and 479.


Example 3: Tick Feeding Assay

Tick nymphs (stage III, Ornithodoros moubata) were fed on artificial membranes with blood spiked with declining concentrations of a test compound (dissolved in a DMSO-emulsifier-blood mixture). Fed nymphs were incubated for around 2-3 weeks to enable tick molting into the next stage. Tick inhibition (i.e, % of damaged+dead ticks at molting-assessment per test concentration) was assessed. The vitality of used parasites was confirmed in negative control groups (i.e., an untreated control and a solvent control).


Results: Compounds with tick activity of 80% inhibition at test concentration of 1 ppm are active, i.e.: Compounds 1, 2, 3, 4, 5, 6, 7, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 469, 470, 471, 472, 473, 474, 475, 477, 478, 479 and 480.


Example 4: Flea Feeding Assay

Adult fleas (Ctenocephalides felis) of defined age were fed on artificial membranes with blood spiked with declining concentrations of a test compound (dissolved in a DMSO-emulsifier-blood mixture). After approximately 48 hours of continuous feeding, flea inhibition (i.e., % of dead+damaged fleas per test concentration) was assessed. The vitality of used parasites was confirmed in negative control groups (i.e., an untreated control and a solvent control).


Results: Compounds with flea activity of 80% inhibition at test concentration of 1 ppm were found active, i.e.: Compounds 4, 15, 18, 19, 20, 21, 23, 24, 25, 64, 65, 80, 81, 86, 87, 88, 89, 90, 91, 95, 99, 100, 115, 145, 149, 150, 160, 173, 179, 183, 184, 185, 197, 200, 203, 209, 212, 213, 220, 221, 223, 227, 230, 252, 265, 278, 281, 289, 309, 313, 321, 331, 333, 335, 352, 376, 379, 386, 423, 432, 469, 470, 471, 472, 473, 474, 475, 477, 478, 479 and 480.


Example 5: Fly Larvae Contact/Feeding Assay

Fly larvae I (Lucilia cuprina) were grown in medium spiked with declining concentrations of a test compound (dissolved in a DMSO-emulsifier-deionized water mixture). Inhibition of fly larvae development (%) was assessed after approximately 48 hours of continuous exposure. The vitality of used parasites was confirmed in negative control groups (i.e., an untreated control and a solvent control).


Results: Compounds with fly larvae activity of 80% inhibition at test concentration of 100 ppm were found active, i.e.: Compounds 3, 4, 5, 6, 8, 14, 18, 19, 20, 21, 26, 46, 49, 50, 51, 55, 56, 59, 63, 64, 65, 69, 80, 81, 86, 87, 88, 90, 91, 95, 99, 100, 101, 107, 113, 114, 115, 136, 145, 147, 149, 150, 169, 171, 173, 179, 183, 184, 185, 197, 200, 203, 209, 212, 213, 215, 216, 220, 221, 223, 227, 230, 233, 252, 264, 265, 278, 281, 284, 289, 294, 309, 310, 313, 321, 331, 335, 352, 376, 379, 386, 423, 432, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479 and 480.


Example 6: Juvenile Sea Lice Contact Assay

Copepodids (juvenile sea lice stage of Lepeophtheirus salmonis) were exposed to seawater spiked with declining concentrations of a test compound (dissolved in a DMSO sea-water mixture). Sea lice inhibition (% of dead+damaged copepodids) was assessed after approximately 24 hours of continuous exposure. The vitality of used parasites was confirmed in a negative (solvent) control group.


Results: The following compounds showed ≥80% inhibition at a test concentration of 100 nM (* denotes 100% inhibition): Compounds 1*, 4, 11*, 27*, 29*, 48*, 51, 63*, 68, 70*, 96*, 98*, 109, 111*, 112*, 124*, 132, 187*, 188*, 189*, 190*, 218*, 454*, 328*, 331*, 335*, 342*, 347*, 355, 364*, 367*, 369*, 370*, 371*, 373*, 375*, 377*, 386*, 405*, 432, 439, 461*, 465*, 466*, 467*, 468*, 470*, 473*, 474*, 480*.


Additionally, the following compounds showed ≥80% inhibition at a test concentration of 10 nM (* denotes 100% inhibition): Compounds 9, 86*, 89*, 447*, 449*, 455*, 456*, 457*, 458*, 459*, 460*, 464*, 469*, 471*, 472, 475*, 477, 478*, 479*.


Additionally, the following compounds showed ≥80% inhibition at a test concentration of 1 nM (* denotes 100% inhibition): Compounds 197*, 446*, 451*, 453*, 463*.


Example 7: Adult Sea Lice Contact Assay

Mobile stages of sea lice (i.e., pre-adults, adults of Lepeophtheirus salmonis) were exposed to seawater spiked with declining concentrations of a test compound (dissolved in a PEG sea-water mixture). Sea lice inhibition (% of dead+damaged sea lice) was assessed after approximately 1 and 24 hours of continuous exposure in comparison to a negative (solvent) control group.


Results: The following compounds had an EC50>10 nM≤25 nM: Compounds 4, 9, 197, 449, 464, 465.


Additionally, the following compound had an EC50≤10 nM: Compounds 8, 86, 89, 446, 447, 451, 453, 454, 455, 456, 457, 458, 459, 460, 463, 466, 469, 471, 473, 474, 475, 477, 478, 479, 480.


Example 8: Adult Caligus rogercresseyi Sea Lice Contact Assay

Mobile stages of sea lice (i.e., pre-adults, adults of Caligus rogercresseyi) were exposed to seawater spiked with declining concentrations of a test compound (dissolved in a PEG sea-water mixture). Sea lice inhibition (% of dead+damaged sea lice) was assessed after approximately 1, 24 and 48 hours of continuous exposure in comparison to a negative (solvent) and untreated control group.


Results: Compound 453 had an EC50 of 0.072 ppb after 24 hours and 0.035 ppb after 48 hours.


Example 9: Tick Larvae Resistance Assay

A tick resistance assay (i.e., larval immersion test, LIT) was carried out using larvae of several Rhipicephalus microplus isolates with known resistance profiles (i.e.: fully susceptible; resistant to dieldrin, coumaphos, DDT, chlorpyriphos, flumethrin, cypermethrin, amitraz, fluazuron).


Tick larvae (Rhipicephalus microplus) were immersed for approximately 3 minutes in test compound solution. Tick mortality was assessed approximately 24 hours after contact exposure. The vitality of used parasites was confirmed in negative control groups (i.e., an untreated control and a solvent control).















Compound 446
Compound 197


Isolate
LC50 (ppm)
LC50 (ppm)

















Fully susceptible
0.344
0.288


DDT, Dieldrin, Coumaphos
0.31
0.346


DDT, Dieldrin, Coumaphos, Chlorpyriphos
0.463
0.335


Coumaphos, Flumethrin, Cypermethrin
0.353
0.343


Coumaphos, Flumethrin, Cypermethrin, Amitraz
0.48
0.375


Dieldrin, Coumaphos, Fluazuron
0.322
0.270





Results: Compounds 446 and 197 were equally effective against the sensitive isolate in comparison to all tested multi-resistant isolates






Example 10: Sea Lice Resistance Assay

A sea lice resistance assay was carried out using mobile sea lice stages (i.e., pre-adults, adults) of several Lepeophtheirus salmonis-isolates with known resistance profiles (i.e.: fully susceptible, resistant to azametiphos (OP), emamectin benzoate (ML), deltamethrin (SP). Sea lice were exposed to seawater spiked with declining concentrations of a test compound (dissolved in a PEG300/sea-water mixture). Sea lice inhibition (% of dead+damaged sea lice) was assessed after approximately 1, 24 and 48 hour/s of continuous exposure in comparison to a negative (solvent) control group.


Results: Compound 453 was equally effective against the sensitive isolate (EC50 1.20 ppb after 24 hours and 0.29 ppb after 48 hours) and the multi-resistant isolate (EC50 1.96 ppb after 24 hours and 0.64 ppb after 48 hours).


In Vivo Assays—Ectoparasites
Example 11: Guinea Pig—Efficacy Against Argaside Tick/Bed Bug

Guinea pigs were locally co-infested (using an infestation device on a shaved skin area) with juvenile soft ticks (Ornithodoros moubata) and bed bugs (Cimex lectularius) before the treatment day (Day 0) to provide a baseline-negative control value. Guinea pigs were treated orally (by gavage) or subcutaneously at a dose of 5 mg/kg bodyweight of a test compound in a formulation of 10% DMF/Emulsifier+90% Aqua ad injectabilia.


Repeated local infestations with both parasites were performed at different time points after treatment. Within approximately 45 min after each infestation ten engorged ticks and ten engorged bed bugs were

    • collected and the percentage of dead and damaged parasites per species were
    • assessed approximately 24 hours following collection. The efficacy was
    • calculated as % of inhibition ‘killed+damaged’ parasites in a treated group in comparison to the baseline-negative control (using a modified Schneider Orelli's formula).


Results: Activity of the test compounds at different evaluation time-points (≥80% inhibition were found active):


Tick Nymphs—Oral Administration

Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on Day 0.


Compounds 4, 51, 86, 197, 447, 451, 453, 466, 469, 470, 471 and 475 showed activity after 7 days.


Compounds 4, 86, 451, 453, 466, 469, 470, 471 and 475 showed activity after 10 days.


Compounds 4, 466, 470, 471, and 475 showed activity after 14 days.


Compounds 470, 471, and 475 showed activity after 17 days.


Compounds 471 showed activity after 21, 24, 28, 31 and 35 days.


Tick Nymphs—Subcutaneous Administration

Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on Day 0.


Compounds 4, 51, 86, 197, 446, 447, 449, 451, 453, 454, 466, 469, 470, 471 and 475 showed activity after 7 days.


Compounds 4, 51, 86, 197, 446, 447, 451, 453, 454, 469, 470, 471 and 475 showed activity after 10 days.


Compounds 4, 51, 446, 447, 469, 470, 471 and 475 showed activity after 14 and 17 days.


Compounds 470, 471 and 475 showed activity after 21, 24, 28 and 31 days.


Compounds 471 and 475 showed activity after 35 days.


Bedbugs—Oral Administration

Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on Day 0.


Compounds 4, 51, 86, 197, 446, 447, 451, 453, 460, 466, 469, 470, 471 and 475 showed activity after 7 days.


Compounds 4, 86, 451, 453, 466, 469, 470, 471 and 475 showed activity after 10 days.


Compounds 4, 466, 470, 471 and 475 showed activity after 14 days.


Compound 466, 470, 471 and 475 showed activity after 17 days.


Compounds 470, 471 and 475 showed activity after 21, 24 and 28 days.


Compounds 471 showed activity after 31 and 35 days.


Bed Bugs—Subcutaneous Administration

Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on Day 0.


Compounds 4, 51, 86, 197, 446, 447, 451, 453, 460, 466, 469, 470, 471 and 475 showed activity after 7 days.


Compounds 4, 51, 86, 197, 446, 447, 451, 453, 466, 469, 470, 471 and 475 showed activity after 10 days.


Compounds 4, 51, 446, 466, 469, 470, 471 and 475 showed activity after 14 and 17 days.


Compounds 446, 469, 470, 471 and 475 showed activity after 21 days.


Compounds 446, 470, 471 and 475 showed activity after 24 days.


Compounds 470, 471 and 475 showed activity after 28 and 31 days.


Compounds 470 and 471 showed activity after 35 days.


Conclusion: The compounds showed efficacy against both parasites and were generally well tolerated in guinea pig.


Compounds 4, 86, 451, 453, 466 and 469 were 100% effective to control ticks and bed bugs at least until Day 10 using both administration routes.


Compounds 4, 470, 471, 475 were 100% effective to control ticks and bed bugs for at least one week using both administration routes.


Subcutaneous administration resulted in a longer duration of efficacy for the compounds 4, 51, 197, 446, 447, 454 and 455.


Example 12: Dog—Efficacy Against Tick/Flea

Beagle dogs were infested (whole body) with 80 Ctenocephalides felis fleas and 50 Rhipicephalus sanguineus or Haemaphysalis elliptica ticks (sex ratio 1:1) two days before the treatment day (Day 0), and repeatedly thereafter. Dogs of treatment groups were treated with 10 mg/kg bodyweight of a test compound orally (compound weighed in gelatin capsule), topically (spot-on, DMA 92%/DEET 8%) or subcutaneously (PEG 200 90%/water for injection 10%). Dogs of the negative control group received only an empty gelatin capsule orally and the spot-on formulation excipients topically.


The efficacy was assessed approximately 48 hours after treatment (assessment of therapeutic efficacy) or 48 hours after each post-treatment infestation (assessment of prophylactic efficacy) by counting live ticks/fleas on dogs in a treatment group in comparison to live parasite counts in the negative control group (efficacy calculation using the Abbott's formula). Compounds with efficacy ≥80 percent were found active.


Ticks—Oral Administration

Compounds 4, 197, 453 and 466 were active on D2 (therapeutic efficacy).


Compound 466 was active up to D16. Compound 453 was active up to D70. Compound 197 was active up to D198.


Ticks—Topical Administration

Compounds 453 and 466 were active on D2 (therapeutic efficacy).


Compound 466 was active up to D30. Compounds 197 and 453 were active up to D70/72.


Ticks—Subcutaneous Administration

Compound 4 was active on D2 (therapeutic efficacy).


Compound 4 was active up to D16.


Fleas—Oral Administration

Compounds 4, 197, 453 and 466 were active on D2 (therapeutic efficacy).


Compounds 453 and 466 were active up to D70. Compound 197 was active up to D227.


Fleas—Topical Administration

Compounds 197, 453 and 466 were active on D2 (therapeutic efficacy).


Compounds 453 and 466 were active up to D70. Compound 197 was active up to D100.


Fleas—Subcutaneous Administration

Compound 4 was active on D2 (therapeutic efficacy).


Compound 4 was active up to D 86.


Conclusion: Compounds showed both therapeutic and prophylactic efficacy against fleas and ticks. They were generally well tolerated in dogs. Compounds 4, 197, 453 and 466 showed therapeutic efficacy against fleas and ticks in dogs.


Compounds 466, 197 and 453 showed prophylactic efficacy against fleas for at least 10 weeks after topical and oral administration.


Compounds 197 and 453 showed prophylactic efficacy against fleas and ticks for at least 10 weeks after topical and oral administration.


Example 13: Cattle—Efficacy Against One-Host Tick

Cattle were infested (whole body) with up to 3000 Rhipicephalus microplus larvae two or three times per week before and after the treatment day (Day 0). Cattle of treatment groups were treated subcutaneously or topically (spray or pour-on) at a dose of 1 mg/kg bodyweight of a test compound. As subcutaneous formulation either 2-pyrrolidon 50%/Tween 80 50% or NMP 60%/PEG300 40% was used. As topical formulation either a spray solution (DMF/Emulsifier 2%/tap water 98%) (Compound 4) or a DMA 92%/DEET 8% pour-on solution (all other compounds) or a pour-on solution containing Imwitor 988 (20%)+Miglyol 840 (QS) (Compound 453 and Compound 466) or a pour-on solution containing Miglyol 840 (QS) (Compound 453) was used. Cattle of the negative control group received only the formulation excipients of the respective administration route.


Fully engorged female ticks dropping from cattle were collected daily after treatment and counted in treatment and control groups. Efficacy was expressed using the standard ADEQ analysis method (ADEQ calculation in accordance with WAAVP guidelines for evaluating the efficacy of acaricides against ticks on ruminants; Veterinary parasitology 136 (2006) 29-43). Compounds with efficacy ≥80 percent were found active/effective. Onset of efficacy means the first Day with efficacy ≥80 percent. Duration of efficacy means the last Day with efficacy ≥80 percent.


Results: Efficacy of the test compounds at different evaluation time-points was as follows:


Compound 4—onset of efficacy on Day 3 after topical administration and on Day 2 after subcutaneous administration.


Compound 446—onset of efficacy on Day 3 after topical administration.


Compound 447—onset of efficacy on Day 4 after topical administration.


Compound 197—onset of efficacy on Day 2 after topical administration and Day 3 after subcutaneous administration.


Compound 453—onset of efficacy after topical (DMA 92%/DEET 8% pour-on solution) and subcutaneous administration on Day 3.


Compound 453 formulated as pour on in Imwitor 988+Miglyol 840—onset of efficacy on Day 1 after topical formulation.


Compound 453 formulated in as pour on in Miglyol 840—onset of efficacy on Day 2 after topical formulation


Compound 466 formulated as pour on in Imwitor 988+Miglyol 840—onset of efficacy on Day 1 after topical administration


Compound 4—duration of efficacy until Day 58 after topical administration (spray solution (DMF/Emulsifier 2%/tap water 98%) and until Day 38 after subcutaneous administration.


Compound 446—duration of efficacy until Day 47 after topical administration.


Compound 447—duration of efficacy at least until Day 57 after topical administration.


Compound 197—duration of efficacy until Day 47 after topical administration and at least until Day 120 after subcutaneous administration.


Compound 453—duration of efficacy until Day 63 after topical administration and until Day 82 after subcutaneous administration.


Compound 453 formulated as pour on in Imwitor 988+Miglyol 840—duration of efficacy until Day 77.


Compound 453 formulated in as pour on in Miglyol 840—duration of efficacy until Day 84.


Compound 466 formulated as pour on in Imwitor 988+Miglyol 840—duration of efficacy until Day 87.


Conclusion: Compounds showed therapeutic efficacy (against existing infestation) and prophylactic efficacy (against re-infestation) against one-host ticks on cattle. They were generally well tolerated in cattle.


Example 14: Cattle—Efficacy Against Multi-Host Ticks

Cattle were treated subcutaneously or topically (pour-on) at a dose of 5 mg/kg bodyweight of a test compound (Day 0). As subcutaneous formulation NMP 60%/PEG300 40% was used, and as pour-on formulation DMA 92%/DEET 8% was used. Cattle of the negative control group received only the formulation excipients of both formulations (SC, pour-on).


Cattle were locally infested with 30 to 40 unfed adult ticks each of Rhipicephalus appendiculatus and Dermacenter variabilis (for both species sex ratio 1:1), by placing the ticks in an ear sleeve (R. appendiculatus) or a stockinet patch attached to the body side (D. variabilis) once before treatment, and at different time points after treatment. Free (i.e., non-attached ticks) were removed from ear sleeves/stockinet patches two days after each infestation and were excluded from the efficacy calculation.


The efficacy (for both tick species) was assessed two days after treatment (assessment of therapeutic efficacy) or three days after each post-treatment infestation (assessment of prophylactic efficacy) by counting of live ticks collected from cattle in a treatment group in comparison to live parasite counts in the negative control group (efficacy calculation using the Abbott's formula). Compounds with efficacy ≥80 percent were found active.


Results: Dermacenter variabilis—Topical Administration


Compounds 197, 446, 447 and 453 showed therapeutic efficacy on Day 2.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 7 days.


Compounds 197, 446 and 453 showed prophylactic efficacy when re-infested after 14 days.


Compounds 197, 446 and 453 showed prophylactic efficacy when re-infested after 21 days.


Compounds 446, 447 and 453 showed prophylactic efficacy when re-infested after 28 days.


Compounds 446 and 453 showed prophylactic efficacy when re-infested after 35 days.



Dermacenter variabilis—Subcutaneous Administration


Compounds 197, 446, 447 and 453 showed therapeutic efficacy on Day 2.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 7 days.


Compounds 197, 446 and 453 showed prophylactic efficacy when re-infested after 14 days.


Compounds 197, 446 and 453 showed prophylactic efficacy when re-infested after 21 days.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 28 days.


Compound 453 showed prophylactic efficacy when re-infested after 35 days.



Rhipicephalus appendiculatus—Topical Administration


Compounds 197, 447 and 453 showed therapeutic efficacy on Day 2.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 7 days.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 14 days.


Compounds 197, 446 and 453 showed prophylactic efficacy when re-infested after 21 days.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 28 days.


Compounds 197, 447 and 453 showed prophylactic efficacy when re-infested after 35 days.



Rhipicephalus appendiculatus—Subcutaneous Administration


Compounds 197, 446, 447 and 453 showed therapeutic efficacy on Day 2.


Compounds 197, 446, and 453 showed prophylactic efficacy when re-infested after 7 days.


Compounds 197, 446 and 453 showed prophylactic efficacy when re-infested after 14 days.


Compounds 197, 446, 447 and 453 showed prophylactic efficacy when re-infested after 21 days.


Compounds 197 and 453 showed prophylactic efficacy when re-infested after 28 days.


Compounds 197 and 453 showed prophylactic efficacy when re-infested after 35 days.


Conclusion: Compounds showed both therapeutic and prophylactic efficacy against multi-host ticks on cattle. They were generally well tolerated in cattle.


Compounds 197, 447 and 453 were 100% effective in treating existing tick infestations using both administration routes.


Example 15: Salmon—In Vivo Efficacy Against Sea Lice Using Gavage Administration

Salmon (Salmo solar) were treated once orally by gavage at a dose of 5 mg/kg bodyweight per fish (Day 0). As formulation DMSO 5%/fish oil 95% was used. Salmon of the negative control group received only the excipients of the formulation.


The fish were infested with Lepeophtheirus salmonis copepodids twice before treatment (i.e., around day −28 and day −3) and once after treatment (i.e., day 17).


At day 7, fish were examined under sedation and (pre-)adult sea lice on each fish were counted and removed (assessment of therapeutic efficacy against (pre-)adult sea lice from day −28 infestation).


Around day 28 (end of animal phase), fish were euthanized, and lice on each fish were classified ((pre-)adult or juvenile stage) and counted. The number of (pre-) adult and juvenile parasite stages corresponding to the respective infestation time point were used for efficacy calculation, i.e., assessment of therapeutic efficacy against juvenile sea lice from day −3 infestation and assessment of prophylactic efficacy from day 17 re-infestation. Efficacy is expressed as a % reduction of sea lice in treated groups versus a control group, using the Abbott's formula.


Results: The following compounds had a therapeutic efficacy of 80% against (pre-)adult sea lice (* denotes 100% efficacy): Compounds 86*, 89*, 197, 449, 451, 453* 459*, 460*. 86*, 89*, 197, 449, 451, 453*, 455*, 456, 457, 458*, 459*, 460*, 463*, 464*, 466, 478*, 479*, 480*.


The following compounds had a therapeutic efficacy of 80% against juvenile sea lice (* denotes 100% efficacy): Compounds 86*, 89*, 449, 459*, 460*. 86*, 89*, 449, 455*, 456*, 457*, 458*, 459*, 460*, 463*, 464*, 466, 478, 479, 480*.


The following compounds had a prophylactic efficacy of 80% at re-infestation on Day 17 (* denotes 100% efficacy): Compounds 453*, 456, 458, 464*.


Example 16: Salmon—In Vivo Efficacy Against Sea Lice Using In-Feed Administration

Four study groups of fish (one group for assessment of therapeutic efficacy, one for assessment of prophylactic efficacy and their respective controls) were used. Commercial fish feed pellets were coated with formulated test compound. As formulation DMSO 5%/fish oil 95% was used. Salmon (Salmo solar) were treated orally with 1 mg/kg fish biomass via coated feed for 7 consecutive days. Salmon of the negative control groups received only feed coated with the excipients of the formulation.


Fish of the therapeutic groups were infested with Lepeophtheirus salmonis copepodids twice before treatment (around day −28 and day −3). Around day 8, fish were examined under sedation and (pre) adult sea lice on each fish were counted and removed (assessment of therapeutic efficacy against (pre-)adult sea lice from around day −28 infestation). Around day 25, fish were euthanized and (pre-) adult sea lice on each fish were counted (assessment of therapeutic efficacy against juvenile sea lice from around day −3 infestation.


Fish of the prophylactic groups were infested at several time points after treatment in 2-week intervals. The fish were assessed for (pre-)adult sea lice approximately 3 weeks after each re-infestation. At each assessment, all (pre-)adult sea lice were removed from the fish. The number of sea lice on fish corresponding to the respective re-infestation time point were used for prophylactic efficacy calculation. Efficacy is expressed as a % reduction of sea lice in treated groups versus a control group using the Abbott's formula.


Results: For Compound 453 100% therapeutic efficacy against (pre-)adult and juvenile sea lice was achieved. Against re-infestation after treatment, prophylactic efficacies were 100% (D14), 99.9% (D28) and 86.0% (D42).


Example 17 Topical Pour-on

All formulations were prepared by weighing the desired amount of either Compound 453 or Compound 466 into a volumetric flask and adding approximately 80% of solvent 1 and all of any additional solvents used or other additives used. The flask was then heated while stirring to a temperature between 5° and 80° C. until the solution was free of any visible solids and then allowed to cool to room temperature. Finally the remainder of solvent 1 was added to the fill line on the volumetric flask.


The table below shows all of the compositions used in the Examples 18 to 20:

















Composition
Compound #
Solvent 1
Solvent 2
Solvent 3
Additive 1







A
453 (1 mg/kg)
Miglyol 840
Imwitor 988 (49%)




B
453 (1 mg/kg
Isopropyl
2-pyrrolidone (35%)
Miglyol 840
L-menthol




Alcohol

(10%)
(10%)


C
453 (1 mg/kg)
Miglyol 840
Imwitor 988 (20%)


D
453 (1 mg/kg)
Miglyol 840
Imwitor 988 (20%)

Oleic Acid







(20%)


E
453 (1 mg/kg)
Miglyol 840
Imwitor 988 (20%)

D-Limonene







(20%)


F
453 (1 mg/kg )
Miglyol 840
Imwitor 988 (20%)

L-Menthol







(20%)


G
453 (1 mg/kg)
Miglyol 840
Imwitor 988 (20%)


H
453 (2.5 mg/kg)
Miglyol 840
Imwitor 988 (20%)


I
466 (1 mg/kg)
Miglyol 840
Imwitor 988 (20%)


J
453 (1 mg/kg)
Miglyol 840





Note:


Number in parenthesis is weight percent of that component. The component in the solvent 1 column is QS to 100% of the composition.






Example 18

Composition A and composition B were each applied to 4 cattle and the concentration of compound 1 (Compound 453) in their blood was monitored over 91 days. FIG. 1 shows how, contrary to many commercially available topical solutions, Compound 1 (453) does not require rapid solvent evaporation on application to have good maximum absorbance (Cmax) and total absorbance (AUC).



FIG. 1 shows that an oily solution (Composition A) had higher Cmax and AUC values of than a volatile solution (Composition B).


Example 19

Compositions C, D, E, and F were each applied to 4 cattle and the concentration of compound 453 in their blood was monitored over 2 days. The data in FIG. 2 below support the claim that no chemical penetration enhancer (CPE) is needed. It is clear that while several of these have slightly higher absorbance and Cmax values, these are not significant improvements and are not enough to impact the overall performance of the compound.



FIG. 2 shows a comparison of concentrations of Compound 453 in the blood of cattle with no CPE (Composition C) and three different CPEs (Compositions D, E, and F) showing no significant improvement with the inclusion of any CPE.


Example 20

Cattle were infested (whole body) with up to 3000 Rhipicephalus microplus larvae two or three times per week before and after the treatment day (Day 0). Cattle of treatment groups were treated topically (pour-on) with the compositions G, H, I and J as disclosed in Example 1. Cattle of the negative control group received only the formulation excipients of the respective administration route.


Fully engorged female ticks dropping from cattle were collected daily after treatment and counted in treatment and control groups. Efficacy was expressed using the standard ADEQ analysis method (ADEQ calculation in accordance with WAAVP guidelines for evaluating the efficacy of acaricides against ticks on ruminants; Veterinary parasitology 136 (2006) 29-43). Compositions with efficacy ≥80 percent were found active/effective. Onset of efficacy means the first Day with efficacy ≥80 percent. Duration of efficacy means the last Day with efficacy ≥80 percent.



FIG. 3 shows the duration of efficacy >90% against R. microplus and the onset of efficacy>90% against R. microplus.


Example 21
In Vitro Test of Rain Fastness

In addition to good absorbance, the composition according to the invention has a high resistance to water. After applying a 5% solution of Compound 453 in Miglyol 840 to rabbit hide and allowing to sit for 4 hours, the sample was soaked in water for 30 minutes. After this there was 4% weight loss and the assaying the water for the presence Compound 453 showed that it was below the detection limit.


Comparative Examples

Compounds that Showed Activity in Prior Art Plant Protection Bioassays but not in Animal Health Parasite Assays


Compounds have been tested in prior art documents WO2016/168059=D1 and WO2018/071327=D2 against a range of plant protection agrochemical relevant parasites. Surprisingly it has been found that a number of compounds from D1 and D2 that were active in plant protection assays did not show activity against animal health parasites in Example 1 described above which is the most sensitive of the assays. The Table below shows the compounds that were not active in against animal health parasites in example 1 with the reference number in such prior art documents and the activity of these compounds in the plant protection bioassays as described below. In particular, these comparative compounds as can be seen, do not have a halogen on the ring formed by A1-A5.


Plant Protection Assays

Bioassays against Beet Armyworm (Spodoptera exigua), Cabbage Looper (Trichoplusia ni) are in the plant protection are a two good indicator species for a broad range of chewing pests. Yellow Fever Mosquito (Aedes aegypti) bioassay is an indicator for sucking pests, including blood sucking pests.


Bioassays on Beet Armyworm BAW (Spodoptera exigua) (“Test A”), and Cabbage Looper CL (Trichoplusia ni) (“Test B”)


Bioassays on BAW: Bioassays on BAW were conducted using a 128-well diet tray assay. One to five second instar BAW larvae were placed in each well (3 mL) of the diet tray that had been previously filled with approximately 1.5 mL of artificial diet to which 50 μg/cm2 of the test molecule (dissolved in 50 μL of 90:10 acetone-water mixture) had been applied (to each of eight wells) and then allowed to dry. Trays were covered with a clear self-adhesive cover, vented to allow gas exchange, and held at 25° C., 14:10 light-dark for five to seven days. Percent mortality was recorded for the larvae in each well; activity in the eight wells was then averaged. The results are indicated in the table below.


Bioassays on CL: Bioassays on CL were conducted using a 128-well diet tray assay. One to five second instar CL larvae were placed in each well (3 mL) of the diet tray that had been previously filled with 1 mL of artificial diet to which 50 μg/cm2 of the test molecule (dissolved in 50 μL of 90:10 acetone-water mixture) had been applied (to each of eight wells) and then allowed to dry. Trays were covered with a clear self-adhesive cover, vented to allow gas exchange, and held at 25° C., 14:10 light-dark for five to seven days. Percent mortality was recorded for the larvae in each well; activity in the eight wells was then averaged. The results are indicated in the table below using the following Test A & B Rating table.












Test A & B Rating Table










% Control (or Mortality)
Rating







50-100
A



More than 0 - Less than 50
B



Not Tested
C



No activity noticed in this bioassay
D











Bioassays on Yellow Fever Mosquito (Aedes aegypti, AEDSAE) (“Test C”).


Master plates containing 400 μg of a molecule dissolved in 100 μL of dimethyl sulfoxide (DMSO) (equivalent to a 4000-ppm solution) are used. A master plate of assembled molecules contains 15 μL per well. To this plate, 135 μL of a 90:10 water/acetone mixture is added to each well. A robot is programmed to dispense 15 μL aspirations from the master plate into an empty 96-well shallow plate (“daughter” plate). There are 6 reps (“daughter” plates) created per master. The created “daughter” plates are then immediately infested with YFM larvae.


The day before plates are to be treated, mosquito eggs are placed in Millipore water containing liver powder to begin hatching (4 g. into 400 mL). After the “daughter” plates are created using the robot, they are infested with 220 μL of the liver powder/larval mosquito mixture (about 1 day-old larvae). After plates are infested with mosquito larvae, a non-evaporative lid is used to cover the plate to reduce drying. Plates are held at room temperature for 3 days prior to grading. After 3 days, each well is observed and scored based on mortality. The results using the following Test C Rating table are indicated in the table below.












Test C Rating Table










% Control (or Mortality)
Rating







80-100
A



More than 0 - Less than 80
B



Not Tested
C



No activity noticed in this bioassay
D












embedded image




    • WO2016/168059=D1

    • WO2018/071327=D2









































comp


#
R2
R3
R4
R12
R13
R14
R15
A
A
B
C
WO
ref







c1
Cl
H
Cl
H
Cl
H
H
4-imidazol-1-ylphenyl
A
A
A
D1
PF56


c2
Cl
H
Cl
H
Cl
H
H
4-(1,2,4-triazol-1-yl)phenyl
A
A
A
D1
PF57


c3
Cl
H
Cl
H
Cl
H
H
2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-
A
A
D
D1
PF60










(trifluoromethyl)ethyl] phenyl


c4
Cl
H
Cl
H
Cl
H
H
4-(cyclopropanecarbonyl amino)phenyl
A
A
A
D1
PF107


c5
Cl
H
Cl
H
Cl
H
H
4-[(2-cyclopropylacetyl)amino]phenyl
A
A
A
D1
PF163


c6
Cl
H
Cl
H
Cl
H
H
4-[[1-(methoxymethyl)cyclo
A
A
A
D1
PF161










propanecarbonyl]amino]phenyl


c7
Cl
H
Cl
H
Cl
H
H
4-[(2,2-
A
A
A
D1
PF108










difluorocyclopropanecarbonyl)amino]phenyl


c8
Cl
H
Cl
H
Cl
H
H
4-(3,3-dimethylbutanoylamino)phenyl
A
A
D
D1
PF164


c9
Cl
H
Cl
H
Cl
H
H
4-(1,2,4-triazol-4-yl)phenyl
A
A
A
D1
PF102


c10
Cl
H
Cl
H
Cl
H
H
4-acetamido-2-methyl-phenyl
A
A
A
D1
PF158


c11
Cl
H
Cl
H
Cl
H
H
1,3-benzothiazol-6-yl
A
A
A
D1
F434


c12
Cl
H
Cl
H
Cl
H
H
1H-indol-5-yl
A
A
A
D1
F435


c13
Cl
H
Cl
H
Cl
H
H
7-quinolyl
A
A
B
D1
F436


c14
Cl
H
Cl
H
Cl
H
H
1H-pyrrolo[3,2-b]pyridin-6-yl
A
A
B
D1
F437


c15
Cl
H
Cl
H
Cl
H
H
2-chloro-3H-benzimidazol-5-yl
A
A
B
D1
F438


c16
Cl
H
Cl
H
Cl
H
H
4-(methoxycarbonylamino)phenyl
A
A
B
D1
PF110


c17
Cl
H
Cl
H
Cl
H
H
5-(trifluoromethyl)-1H-pyrazol-3-yl
A
A
D
D1
PF138


c18
Cl
H
Cl
H
Cl
H
H
4-pyrazol-1-ylphenyl
A
A
A
D1
F440


c19
Cl
H
Cl
H
Cl
H
H
2-Benzthiazolyl
A
A
B
D1
F441


c20
Cl
OMe
Cl
H
Cl
H
H
4-acetamidophenyl
A
A
D
D1
F181


c21
Cl
OMe
Cl
H
Cl
H
H
4-(methylamino)phenyl
A
A
D
D1
F182


c22
Cl
H
Cl
H
Cl
H
H
1H-tetrazol-5-yl
A
A
B
D1
PF130


c23
Cl
H
Cl
H
Cl
H
H
4-oxazol-2-ylphenyl
A
A
D
D1
F446


c24
Cl
H
Cl
H
Cl
H
H
4-(p-tolyl)thiazol-2-yl
A
A
D
D1
PF136


c25
Cl
H
Cl
H
Cl
H
H
2,4-dioxo-1H-pyrimidin-5-yl
A
A
B
D1
PF139


c26
Cl
H
Cl
H
Cl
H
H
2-Benzoxazolyl
A
A
A
D1
F447


c27
Cl
H
Cl
H
Cl
H
H
1,3-benzoxazol-6-yl
A
A
A
D1
F450


c28
Cl
H
Cl
H
Cl
H
H
benzothiophen-5-yl
A
A
A
D1
F452


c29
Cl
H
Cl
H
Cl
H
H
3-aminophenyl
A
A
A
D1
F201


c30
Cl
H
Cl
H
Cl
H
H
3-(methylamino)phenyl
A
A
A
D1
F202


c31
Cl
H
Cl
H
Cl
H
H
3-amino-4-methyl-phenyl
A
A
B
D1
F205


c32
Cl
H
Cl
H
Cl
H
H
2-methyl-1H-indol-5-yl
A
A
A
D1
F454


c33
Cl
H
Cl
H
Cl
H
H
2-methyl-1,3-benzothiazol-5-yl
A
A
A
D1
F455


c34
Cl
H
Cl
H
Cl
H
H
1H-benzimidazol-5-yl
A
A
B
D1
F456


c35
Cl
H
Cl
H
Cl
H
H
2-methyl-4-(methylamino)phenyl
A
A
A
D1
F196


c36
Cl
H
Cl
H
Cl
H
H
1-methylindol-5-yl
A
A
A
D1
F457


c37
Cl
H
Cl
H
Cl
H
H
1-benzylindol-5-yl
A
A
D
D1
F458


c38
Cl
H
Cl
H
Cl
H
H
1-methyl-2-oxo-indolin-5-yl
A
A
A
D1
F459


c39
Cl
H
Cl
H
Cl
H
H
1-methyl-5-(trifluoromethyl)indazol-3-yl
A
A
A
D1
F460


c40
Cl
H
Cl
H
Cl
H
H
4-(triazol-1-yl)phenyl
A
A
B
D1
F217


c41
Cl
H
Cl
H
Cl
H
H
4-thiazol-2-ylphenyl
A
A
A
D1
F461


c42
H
F
Cl
H
Cl
H
H
4-[tert-butoxycarbonyl(methyl)amino]-
A
D
D
D1
F219










2-methyl-phenyl


c43
Cl
H
Cl
H
Cl
H
Me
4-[tert-butoxycarbonyl(methyl)amino]-
A
A
D
D1
F220










2-methyl-phenyl


c44
Cl
Cl
Cl
H
Cl
H
Me
4-[tert-butoxycarbonyl(methyl)amino]-
A
D
D
D1
F221










2-methyl-pheny


c45
Cl
H
Cl
H
Cl
H
H
4-(2-thienyl)thiazol-2-yl
A
A
A
D1
PF135


c46
Cl
H
Cl
H
Cl
H
H
2-(trifluoromethyl)-1H-indol-5-yl
A
A
D
D1
F465


c47
Cl
Cl
Cl
H
Cl
H
H
2-methyl-4-(methylamino)phenyl
A
A
A
D1
F223


c48
Cl
H
Cl
H
Cl
H
Me
2-methyl-4-(methylamino)phenyl
A
A
D
D1
F225


c49
Cl
Cl
Cl
H
Cl
H
Me
2-methyl-4-(methylamino)phenyl
A
A
A
D1
F226


c50
H
F
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F228


c51
Cl
H
Cl
H
Cl
H
H
2-cyano-4-nitro-phenyl
A
A
A
D1
F229


c52
Cl
H
Cl
H
Cl
H
H
4-methyl-2-nitro-phenyl
A
A
A
D1
F231


c53
Cl
H
Cl
H
Cl
H
H
2-cyano-4-(trifluoromethyl)phenyl
A
A
A
D1
F232


c54
Cl
H
Cl
H
Cl
H
H
4-cyano-3-(trifluoromethyl)phenyl
A
A
A
D1
F235


c55
Cl
H
Cl
H
Cl
H
H
1,3-dioxoisoindolin-5-yl
A
A
D
D1
F439


c56
Cl
H
Cl
H
Cl
H
H
4-amino-2-cyano-phenyl
A
A
A
D1
F236


c57
Cl
H
Cl
H
Cl
H
H
2-cyano-4-(diacetylamino)phenyl
A
A
A
D1
F469


c58
Cl
H
Cl
H
Cl
H
H
2-cyano-4-(methylamino)phenyl
A
A
A
D1
F237


c59
Cl
H
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F195


c60
Cl
H
Cl
H
Cl
H
H
2-oxoindolin-5-yl
A
A
A
D1
F472


c61
Cl
H
Cl
H
Cl
H
H
1H-pyrrolo[2,3-c]pyridin-5-yl
A
A
A
D1
F474


c62
Cl
H
Cl
H
Cl
H
H
imidazo[1,2-a]pyridin-6-yl
A
A
A
D1
F475


c63
Cl
H
Cl
H
Cl
H
H
1-methylpyrazolo[3,4-b]pyridin-5-yl
A
A
A
D1
F476


c64
Cl
H
Cl
H
Cl
H
H
6-methyl-1H-indazol-3-yl
A
A
A
D1
F478


c65
Cl
H
Cl
H
Cl
H
H
4-(2,5-dioxopyrrol-1-yl)-2-methyl-phenyl
A
A
A
D1
F480


c66
Cl
H
Cl
H
Cl
H
H
1H-pyrrolo[2,3-b]pyridin-5-yl
A
A
A
D1
F481


c67
Cl
H
Cl
H
Cl
H
H
2-ethoxycarbonyl-1H-indol-5-yl
A
A
A
D1
F483


c68
Cl
H
Cl
H
Cl
H
H
1-tert-butoxycarbonylindol-5-yl
A
A
D
D1
F484


c69
Cl
H
Cl
H
Cl
H
H
4-methyl-1H-indol-5-yl
A
A
A
D1
F485


c70
Cl
H
Cl
H
Cl
H
H
2-tert-butyl-1H-indol-5-yl
A
A
A
D1
F486


c71
Cl
H
Cl
H
Cl
H
H
2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-
A
A
A
D1
F257










methoxycarbonyl-ethyl)phenyl


c72
Cl
H
Cl
H
Cl
H
H
2-methyl-4-[1-(trifluoromethyl)vinyl]phenyl
A
A
B
D1
F258


c73
Cl
H
Cl
H
Cl
H
H
1-ethylindol-5-yl
A
A
A
D1
F488


c74
Cl
Cl
Cl
H
H
H
H
4-(tert-butoxycarbonylamino)-
A
A
B
D1
F262










2-methyl-phenyl


c75
Cl
H
Cl
H
H
H
H
4-(tert-butoxycarbonylamino)-
A
A
B
D1
F263










2-methyl-phenyl


c76
Cl
Cl
Cl
H
H
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F264


c77
Cl
Cl
H
H
H
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F265


c78
Cl
H
Cl
H
H
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F266


c79
Cl
H
Cl
Cl
Cl
H
H
Phenyl
A
A
A
D1
F246


c80
Cl
H
Cl
Cl
Cl
H
H
4-(methylamino)phenyl
A
A
A
D1
F249


c81
Cl
H
Cl
H
Cl
H
H
4-(tert-butoxycarbonylamino)-
A
A
A
D1
F275










2-methyl-phenyl


c82
Cl
H
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F283


c83
Cl
H
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F284


c84
Cl
Cl
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F286


c85
Cl
H
Cl
H
Cl
H
H
2,4-dicyanophenyl
A
A
A
D1
F287


c86
Cl
H
Cl
H
Cl
H
H
1-methyl-2-oxo-3,4-dihydroquinolin-6-yl
A
A
A
D1
F490


c87
Cl
H
Cl
H
Cl
H
H
1-methyl-3,4-dihydro-2H-quinolin-6-yl
A
A
A
D1
F491


c88
Cl
H
Cl
H
Cl
H
H
1,2,3,4-tetrahydroquinolin-6-yl
A
A
A
D1
F492


c89
Cl
F
H
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F291


c90
Cl
H
Cl
H
Cl
H
H
6-acetamido-2-pyridyl
A
A
A
D1
F494


c91
Cl
H
Cl
H
Cl
H
H
6-amino-5-cyano-2-pyridyl
A
A
D
D1
F292


c92
Cl
H
Cl
H
Cl
H
H
4-(N-cyano-S-methyl-sulfinimidoyl)phenyl
A
A
A
D1
F495


c93
Cl
H
Cl
H
Cl
H
H
1-(2-fluoroethyl)indol-5-yl
A
A
A
D1
F496


c94
Cl
H
Cl
H
Cl
H
H
2-phenyl-1H-indol-5-yl
A
A
A
D1
F497


c95
Cl
H
Cl
H
Cl
H
H
2-cyano-3-methyl-phenyl
A
A
A
D1
F304


c96
Cl
H
Cl
H
Cl
H
H
2-methylisoindolin-5-yl
A
A
A
D1
F498


c97
Cl
H
Cl
H
Cl
H
H
6-(tert-butoxycarbonylamino)-2-pyridyl
A
A
D
D1
F505


c98
Cl
F
H
H
Cl
H
H
6-(tert-butoxycarbonylamino)-2-pyridyl
A
A
A
D1
F506


c99
Cl
H
Cl
H
Cl
H
H
indolin-5-yl
A
A
A
D1
F511


c100
H
Br
Cl
H
Cl
H
H
2-methyl-4-(methylamino)phenyl
A
A
A
D1
F323


c101
H
Br
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F324


c102
Cl
H
Br
H
Cl
H
H
4-(tert-butoxycarbonylamino)-
A
A
D
D1
F335










2-methyl-phenyl


c103
Br
H
Cl
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F337


c104
Cl
H
Cl
H
Cl
H
H
2-methyl-3-oxo-isoindolin-5-yl
A
A
A
D1
F517


c105
Cl
H
Cl
H
Cl
H
H
2-methyl-1-oxo-isoindolin-5-yl
A
A
A
D1
F518


c106
Cl
H
Cl
H
Cl
H
H
5-nitro-3-pyridyl
A
A
A
D1
F358


c107
Cl
Cl
H
H
Cl
H
H
5-nitro-3-pyridyl
A
A
A
D1
F359


c108
Cl
H
Cl
H
Cl
H
H
5-(hydroxyamino)-3-pyridyl
A
A
A
D1
F525


c109
Cl
H
Cl
H
Cl
H
H
5-amino-3-pyridyl
A
A
A
D1
F362


c110
Cl
Cl
H
H
Cl
H
H
5-(hydroxyamino)-3-pyridyl
A
A
A
D1
F526


c111
Cl
Cl
H
H
Cl
H
H
5-amino-3-pyridyl
A
A
A
D1
F363


c112
Cl
H
Cl
H
Cl
H
H
1-methylindol-4-yl
A
A
A
D1
F530


c113
Cl
H
Cl
H
Cl
H
H
1-methylindol-7-yl
A
A
A
D1
F531


c114
Cl
Cl
H
H
Cl
H
H
4-amino-2-methyl-phenyl
A
A
A
D1
F574


c115
Cl
H
Cl
H
Cl
H
H
4-[(2-methoxyacetyl)-methyl-amino]phenyl
A
A
B
D1
PF31


c116
Cl
H
Cl
H
Cl
H
H
3-methyl-4-(methylamino)phenyl
A
A
A
D1
F206


c117
H
F
Cl
H
Cl
H
H
4-acetamidophenyl
A
A
A
D1
F260


c118
Cl
F
H
Cl
Me
H
H
4-acetamidophenyl
A
A
A
D2
F1191


c119
CF3
F
H
H
Cl
H
H
4-(2-acetoxyethylamino)-2-methyl-phenyl
A
A
C
D2
F1144


c120
CF3
F
H
H
Cl
H
H
4-(2-hydroxyethylamino)-2-methyl-phenyl
A
A
C
D2
F1145


c121
Cl
F
H
CF3
Cl
H
H
Phenyl
A
A
A
D2
F1212


c122
Cl
F
H
H
Cl
Cl
H
Phenyl
A
A
A
D2
F1104


c123
H
F
CF3
H
Cl
H
H
4-amino-2,3-dimethyl-phenyl
A
A
A
D2
F1389


c124
H
F
CF3
H
Cl
H
H
2,3-dimethyl-4-[(2,2,2-
A
A
A
D2
F1392










trifluoroacetyl)amino]phenyl


c125
H
F
CF3
H
Cl
H
H
2-methyl-3-[(2,2,2-
A
A
A
D2
F1451










trifluoroacetyl)amino]phenyl








Claims
  • 1. A method of treatment or control of a parasitic infestation of an animal comprising administering to an animal a Compound of Formula (I)
  • 2. A method of treatment or control of a parasitic infestation according to claim 1, wherein at least two of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.
  • 3. A method of treatment or control of a parasitic infestation according to claim 1, wherein 1 of A1, A2, A3, A4, A5 is N.
  • 4. A method of treatment or control of a parasitic infestation according tom claim 1, wherein R12 is selected from the group consisting of H, F, CL, CH3, and CF3.
  • 5. A method of treatment or control of a parasitic infestation according to claim 1, wherein R13 is selected from the group consisting of H, F, Cl, CF3 and CH3.
  • 6. A method of treatment or control of a parasitic infestation according to claim 1, wherein R15 is selected from the group consisting of H and CH3.
  • 7. A method of treatment or control of a parasitic infestation according to claim 1, wherein at least one of the following selections is made: R1 is selected from the group consisting of H F, and Cl; orR2 is selected from the group consisting of H, F, and Cl; orR3 is selected from the group consisting of H, F, and Cl; orR4 is selected from the group consisting of H, F, and Cl.
  • 8. A method of treatment or control of a parasitic infestation according to claim 1, wherein at least one of the following selections is made: R5 is selected from the group consisting of H F, Cl, Br, and I; orR6 is selected from the group consisting of H, F, and Cl, Br, and CH3; orR7 is selected from the group consisting of H F, Cl, Br, and I; orR8 is selected from the group consisting of H, F, Cl, and Br, and CH3; orR9 is selected from the group consisting of H F, Cl, Br, and I.
  • 9. A method of treatment or control of a parasitic infestation according to claim 1, wherein: R1 is selected from the group consisting of H F, and Cl;R2 is selected from the group consisting of H, F, and Cl;R3 is selected from the group consisting of H, F, and Cl;R4 is selected from the group consisting of H, F, and Cl;R5 is selected from the group consisting of H F, Cl, Br, and I;R6 is selected from the group consisting of H, F, and Cl, Br, and CH3;R7 is selected from the group consisting of H F, Cl, Br, and I;R8 is selected from the group consisting of H, F, Cl, and Br, and CH3;R9 is selected from the group consisting of H F, Cl, Br, and I;R11 is H;R12 is selected from the group consisting H, F, CL, CH3, CF3;R13 is selected from the group consisting of H, F, Cl, CF3 and CH3;R14 is H or F;R15 is selected from the group consisting of H and CH3; andwherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.
  • 10. A method of treatment or control of a parasitic infestation according to claim 1, wherein: R1 is H;R2 is selected from the group consisting of H, F, and Cl;R3 is selected from the group consisting of H, Cl, F, and Br;R4 is H, F, Cl;R5 is selected from the group consisting of H F, and Cl;R6 is selected from the group consisting of H, F, and Cl, and CH3;R7 is selected from the group consisting of H F, and Cl;R8 is selected from the group consisting of H, F, Cl, and CH3;R9 is selected from the group consisting of H F, and Cl;R11 is H;R12 is selected from the group consisting H, F and Cl;R13 is selected from the group consisting of H, F, and Cl;R14 is H;R15 is selected from the group consisting of H and CH3; andwherein at least one of R5, R6, R7, R8, R9, is a substituent selected from the group consisting of F, Cl, Br, and I.
  • 11. A method of treatment or control of a parasitic infestation according to claim 1, wherein the parasitic infestation is an ectoparasite infestation.
  • 12. A method of treatment or control of a parasitic infestation according to claim 1, wherein the parasitic infestation is an acaracide infestation.
  • 13. A method of treatment or control of a parasitic infestation according to claim 1, wherein the parasitic infestation is an infestation selected from tick, flea or fly.
  • 14. A method of treatment or control of a parasitic infestation according to claim 1, wherein the parasite is a one host tick or a multi-host tick.
  • 15. A method of treatment or control of a parasitic infestation according to claim 1, wherein the animal is a warm-blooded animal.
  • 16. A method of treatment or control of a parasitic infestation according to claim 1, wherein the animal is a livestock animal.
  • 17. A method of treatment or control of a parasitic infestation according to claim 1, wherein the animal is a fish, and the parasitic infestation is a sea lice infestation.
  • 18. A method of treatment or control of a parasitic infestation according to claim 1, wherein the animal is a companion animal.
  • 19. A method of treatment or control of a parasitic infestation according to claim 1, wherein the animal is protected from a parasite infestation.
  • 20. A method of treatment or control of a parasitic infestation Compound for use according to claim 1, wherein an existing parasite infestation of the animal is treated or controlled.
  • 21. A method of treatment or control of a parasitic infestation according to claim 1, wherein the method comprises administering the compound to an animal weekly, bi-weekly, monthly, every 6 weeks, every 2 months, every 3 months, 6 months or 9 months.
  • 22. A method of treatment or control of a parasitic infestation according to claim 1 wherein the compound is a compound of Formula
  • 23. A veterinary composition comprising an effective amount of a compound of Formula (I) as defined in claim 1 and an inert carrier or formulation adjuvant.
  • 24. The veterinary composition according to claim 23, wherein the veterinary composition is a topical composition, an oral composition, or an injection composition.
  • 25. The veterinary composition according to claim 23 and a pharmaceutically acceptable oily carrier.
  • 26. The veterinary composition according to claim 25 wherein the oily carrier comprises a fatty acid ester.
  • 27. The veterinary pharmaceutical composition according to claim 26, wherein the fatty acid ester is a glycol diester or a glycerol triester of a C8-10 fatty acid.
  • 28. The veterinary pharmaceutical composition according to claim 25, wherein the oily carrier comprises a combination of glycerol monocaprylate and propylene glycol dicaprylocaprate.
  • 29. The veterinary pharmaceutical composition according to claim 23, wherein the composition does not comprise a penetration enhancer.
  • 30. The veterinary pharmaceutical composition according to claim 23, comprising: a) from about 0.5% to about 10% w/v of the compound of Formula (I);b1) from about 90% to 99.9% w/v of propylene glycol octanoate decanoate; or alternativelyb2) from about 10% to about 40% w/v, of glycerol monocaprylate; andc) optionally, from about 2% to about 50% w/v, of propylene glycol dicaprylocaprate.
  • 31. A Compound of Formula
Priority Claims (1)
Number Date Country Kind
21153638.8 Jan 2021 EP regional
PCT Information
Filing Document Filing Date Country Kind
PCT/EP2022/051674 1/26/2022 WO
Provisional Applications (1)
Number Date Country
63292561 Dec 2021 US